- N-Alkoxy Carboxamide Stabilized Tin(II) and Germanium(II) Complexes for Thin-Film Applications
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A new series of germanium (1–5) and tin (6–10) complexes were successfully synthesized by employing N-alkoxy-functionalized carboxamides as stabilizing ligands, and these complexes could potentially serve as precursors for thin-film applications. All of t
- George, Sheby Mary,Nam, Ji Hyeun,Lee, Ga Yeon,Han, Jeong Hwan,Park, Bo Keun,Kim, Chang Gyoun,Jeon, Dong Ju,Chung, Taek-Mo
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- Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C-H/N-H annulation of N -methoxy benzamides with saturated ketones
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The synthesis of isoindolinones from N-methoxy benzamides and saturated ketones via a bimetallic tandem catalytic annulation has been accomplished. The reaction is catalyzed by a Rh/Cu-cocatalytic system and proceeds via the combination of Cu-catalyzed de
- Du, Xiao,Hu, Yuntao,Huang, Decai,Wu, Hailong,Yang, Darun,Yang, Wendi,Zhao, Huaiqing
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supporting information
p. 783 - 789
(2022/02/03)
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- Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
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The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
- Tóth, Balázs L.,Sályi, Gerg?,Domján, Attila,Egyed, Orsolya,Bényei, Attila,Gonda, Zsombor,Novák, Zoltán
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p. 348 - 354
(2021/11/09)
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- Pd(II)-catalyzed annulation reactions of epoxides with benzamides to synthesize isoquinolones
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Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C?H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.
- Wang, Huihong,Cao, Fei,Gao, Weiwei,Wang, Xiaodong,Yang, Yuhang,Shi, Tao,Wang, Zhen
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supporting information
p. 863 - 868
(2021/02/06)
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- Pd/C-catalyzed aerobic oxidative C–H alkenylation of arenes in γ-valerolactone (GVL)
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A novel methodology for the heterogeneous palladium-catalyzed C–H alkenylation of N-methoxybenzamides and anilides is presented. This approach is based on the use of commercially available Pd/C as catalyst and molecular oxygen as terminal oxidant, in comb
- Anastasiou, Ioannis,Ferlin, Francesco,Santoro, Stefano,Vaccaro, Luigi,Viteritti, Orlando
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- Electrodimerization ofN-Alkoxyamides for the Synthesis of Hydrazines
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An efficient and valuable N-N dimerization reaction ofN-alkoxyamides is reported under undivided electrolytic conditions. This electrochemical strategy provides a powerful way to access a wide range of advanced, highly functionalized hydrazines. Remarkably, anN-centered radical generated from the cleavage of the N-H bond under electrolytic conditions plays a crucial role in this transformation. Furthermore, variousN-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.
- Nasier, Abudulajiang,Chang, Xihao,Guo, Chang
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p. 16068 - 16076
(2021/09/18)
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- Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature
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Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is
- Nielsen, John,Tung, Truong Thanh
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supporting information
p. 10073 - 10080
(2021/12/10)
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- Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides
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The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.
- Zhang, Xinyu,Lin, Bo,Chen, Jianhui,Chen, Jiajia,Luo, Yanshu,Xia, Yuanzhi
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supporting information
p. 819 - 825
(2021/02/01)
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- Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of: N -methoxybenzamides with a Rh(iii)-catalyst
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Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.
- Mayakrishnan, Sivakalai,Tamizmani, Masilamani,Maheswari, Naryanan Uma
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supporting information
p. 15462 - 15465
(2020/12/25)
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- Cp?CoIII-catalyzed formal [4+2] cycloaddition of benzamides to afford quinazolinone derivatives
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A Cp?CoIII-catalyzed arene C-H bond amidation/annulation of benzamides was developed to afford quinazolinone derivatives in one-pot with high yields and broad substrate scope. This method could be applied to the synthesis of quinazolinone drugs and late-stage modification of natural products.
- Yang, Jingshu,Hu, Xiao,Liu, Zijie,Li, Xueyuan,Dong, Yi,Liu, Gang
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supporting information
p. 13840 - 13843
(2019/11/21)
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- Three-Component Synthesis of Isoquinoline Derivatives by a Relay Catalysis with a Single Rhodium(III) Catalyst
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A rhodium(III)-catalyzed one-pot three-component reaction of N-methoxybenzamide, α-diazoester, and alkyne was developed, providing an alternative way to synthesize isoquinoline derivatives. Mechanistically, it is a relay catalysis, and the reaction occurred via successive O-alkylation and C-H activation processes, both of which were promoted by the same catalyst.
- Zhou, Chao,Jiang, Jijun,Wang, Jun
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supporting information
p. 4971 - 4975
(2019/09/03)
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- Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent
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The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.
- Yang, Qi-Liang,Wang, Xiang-Yang,Wang, Tong-Lin,Yang, Xiang,Liu, Dong,Tong, Xiaofeng,Wu, Xin-Yan,Mei, Tian-Sheng
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supporting information
p. 2645 - 2649
(2019/04/17)
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- Palladium-Catalyzed Inert C?H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1-b]isoquinoline-5,7-Diones
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A palladium-catalyzed inert C?H bond activation and cyclocarbonylation of isoquinolones leading to isoindolo[2,1-b]isoquinoline-5,7-diones under 1 atm of carbon dioxide has been developed. This transformation features high regio- and chemo-selectivity, step-economy, and good functional group tolerance. Most of the corresponding products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse isoindolo[2,1-b]isoquinoline-5,7-dione derivatives. (Figure presented.).
- Yan, Kelu,Jin, Junbin,Kong, Yong,Li, Bin,Wang, Baiquan
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supporting information
p. 3080 - 3085
(2019/05/21)
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- Controllable construction of isoquinolinedione and isocoumarin scaffolds: Via RhIII-catalyzed C-H annulation of N -tosylbenzamides with diazo compounds
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A highly efficient protocol for the synthesis of isoquinolinediones by RhIII-catalyzed C-H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C-H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.
- Liu, Yanfei,Wu, Jiaping,Qian, Baiyang,Shang, Yongjia
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supporting information
p. 8768 - 8777
(2019/10/16)
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- Pd(II)-Catalyzed asymmetric oxidative annulation of N-alkoxyheteroaryl amides and 1,3-dienes
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The first Pd(II)-catalyzed asymmetric oxidative annulation of N-alkoxyaryl amides and 1,3-dienes is reported, which features particular applicability for quick assembly of different types of chiral heterocycles with high yields and enantioselectivities. A novel chiral pyridine-oxazoline bearing a methoxyl group at the C-5 position and a gem-dimethyl group on the oxazoline moiety was found to be crucial for conversion.
- Zhang, Tao,Shen, Hong-Cheng,Xu, Jia-Cheng,Fan, Tao,Han, Zhi-Yong,Gong, Liu-Zhu
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supporting information
p. 2048 - 2051
(2019/03/29)
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- Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation
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The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.
- Jia, Bing,Yang, Yunhui,Jin, Xiqing,Mao, Guoliang,Wang, Congyang
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p. 6259 - 6263
(2019/09/06)
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- Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (E)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant
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Regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones via Pd(II)/Cu(II)-catalyzed one-pot C-C/C-N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency. Further elaboration of the products obtained from this process enabled very short and efficient syntheses of aristolactam and indoloisoquinolinone alkaloids.
- Youn, So Won,Ko, Tae Yun,Kim, Young Ho,Kim, Yun Ah
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supporting information
p. 7869 - 7874
(2019/01/14)
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- Rhodium(III)-catalyzed chemodivergent annulations between: N-methoxybenzamides and sulfoxonium ylides via C-H activation
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Chemodivergent and redox-neutral annulations between N-methoxybenzamides and sulfoxonium ylides have been realized via Rh(iii)-catalyzed C-H activation. The sulfoxonium ylide acts as a carbene precursor, and coupling occurs under acid-controlled condition
- Xu, Youwei,Zheng, Guangfan,Yang, Xifa,Li, Xingwei
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supporting information
p. 670 - 673
(2018/01/28)
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- Catalytic Alkene Difunctionalization via Imidate Radicals
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The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The broad scope and utility of this catalytic method for imidate radical reactivity is presented, along with comparisons to other N-centered radicals and complementary, closed-shell imidate pathways.
- Nakafuku, Kohki M.,Fosu, Stacy C.,Nagib, David A.
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supporting information
p. 11202 - 11205
(2018/09/12)
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- Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung
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The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.
- Caramenti, Paola,Nicolai, Stefano,Waser, Jerome
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supporting information
p. 14702 - 14706
(2017/09/11)
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- Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones
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A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).
- Sharma, Nidhi,Saha, Rajib,Parveen, Naziya,Sekar, Govindasamy
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supporting information
p. 1947 - 1958
(2017/06/09)
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- C-F bond cleavage enabled redox-neutral [4+1] annulation via C-H bond activation
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Using α,α-difluoromethylene alkyne as a nontraditional one-carbon reaction partner, a synthetically novel method for the construction of isoindolin-1-one derivatives via Rh(III)-catalyzed [4+1] annulation reaction is reported. The 2-fold C-F bond cleavage not only enables the generation of desired product under an overall oxidant-free condition but also results in a net migration of carbon-carbon triple bond. In addition, the present reaction protocol exhibits a tolerance of a wide spectrum of functional groups due to the mild reaction conditions employed.
- Wang, Cheng-Qiang,Ye, Lu,Feng, Chao,Loh, Teck-Peng
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supporting information
p. 1762 - 1765
(2017/02/15)
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- Selective mono-alkylation of N-methoxybenzamides
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We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared 30 mono-alkylated aryl amides in good yields with good mono-selectivity. We have also demonstrated that structurally rigid alkenes such as norbornene and its derivatives are a good class of ligand and could be used for future direct C-H functionalizations. The utilization of norbornene type ligands for assistance in C-H activation processes has opened a new window for future molecular design using direct C-H functionalization strategies.
- Chen, Zenghua,Hu, Le'an,Zeng, Fanyun,Zhu, Ranran,Zheng, Shasha,Yu, Qingzhen,Huang, Jianhui
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supporting information
p. 4258 - 4261
(2017/04/21)
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- Method for preparing isoquinoline dione from methoxybenzamide and diazotate ester through carbon-hydrogen functionalization
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The invention discloses a method for preparing isoquinoline dione from methoxybenzamide and diazotate ester through carbon-hydrogen functionalization, which comprises the following steps: (1) reacting in a solvent under protection of an inert gas at 100+/
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Paragraph 0031-0033
(2017/11/04)
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- Ir(III)-Catalyzed Carbenoid Functionalization of Benzamides: Synthesis of N-Methoxyisoquinolinediones and N-Methoxyisoquinolinones
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A mild and efficient Ir(III)-catalyzed C-H carbenoid functionalization strategy has been developed to access N-methoxyisoquinolinediones and N-methoxyisoquinolinones. The reaction proceeds efficiently in high yield at room temperature over a broad range of substrates without requirement of any additional oxidants or a base.
- Phatake, Ravindra S.,Patel, Pitambar,Ramana, Chepuri V.
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supporting information
p. 2828 - 2831
(2016/07/06)
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- Rh-Catalyzed annulations of: N -methoxybenzamides with ketenimines: Synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones with strong aggregation induced emission properties
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Rhodium-catalyzed C-H activation/annulation reactions of ketenimines with N-methoxybenzamides furnished 3-aminoisoindolin-1-ones and 3-(diarylmethylene)isoindolin-1-ones. The synthesized 3-(diarylmethylene)isoindolin-1-ones exhibited aggregation induced emissions in aqueous tetrahydrofuran solution and strong green-yellow emissions in solids.
- Zhou, Xiaorong,Peng, Zhixing,Zhao, Hongyang,Zhang, Zhiyin,Lu, Ping,Wang, Yanguang
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supporting information
p. 10676 - 10679
(2016/09/02)
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- Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols to Form γ-Lactams via Rhodium(III)-Catalyzed C-H Activation
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A mild, regiocontrolled coupling of aromatic and vinylic amides with α-allenols to form γ-lactams via rhodium(III)-catalyzed C-H activation has been demonstrated. This [4 + 1] annulation reaction provides an efficient method for the synthesis of isoindolinones and 1,5-dihydro-pyrrol-2-ones bearing a tetrasubstituted carbon atom α to the nitrogen atom with good functional group tolerance. The hydroxyl group in the allene substrate is essential in controlling the chemo- and regioselectivity of the reaction probably by coordination interaction with the rhodium catalyst.
- Zhou, Zhi,Liu, Guixia,Lu, Xiyan
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supporting information
p. 5668 - 5671
(2016/11/17)
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- Palladium-Catalyzed Deaminative Phenanthridinone Synthesis from Aniline via C-H Bond Activation
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This work reports palladium-catalyzed phenanthridinone synthesis using the coupling of aniline and amide by formation of C-C and C-N bonds in a one-pot fashion via dual C-H bond activation. It involves simultaneous cleavage of four bonds and the formation of two new bonds. The present protocol is ligand-free, takes place under mild reaction conditions, and is environmentally benign as nitrogen gas and water are the only side products. This transformation demonstrates a broad range of aniline and amide substrates with different functional groups and has been scaled up to gram level.
- Yedage, Subhash L.,Bhanage, Bhalchandra M.
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supporting information
p. 4103 - 4111
(2016/06/09)
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- Rhodium(iii)-catalyzed C-H/C-C activation sequence: Vinylcyclopropanes as versatile synthons in direct C-H allylation reactions
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Succession of C-H activation and C-C activation was achieved by using a single rhodium(iii) catalyst. Vinylcyclopropanes were used as versatile coupling partners. Mechanistic studies suggest that the olefin insertion step is rate-determining and a facile β-carbon elimination is involved, which represents a novel ring opening mode of vinylcyclopropanes. This journal is
- Wu, Jia-Qiang,Qiu, Zhi-Ping,Zhang, Shang-Shi,Liu, Jing-Gong,Lao, Ye-Xing,Gu, Lian-Quan,Huang, Zhi-Shu,Li, Juan,Wang, Honggen
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supporting information
p. 77 - 80
(2015/01/09)
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- Amides and Ethers as Chemoselective Surrogates for Copper(II)-Catalyzed ortho Benzoyloxylation of 2-Phenylpyridines
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Chemoselective ortho benzoyloxylation of 2-phenylpyridine derivatives using amides and ethers as novel arylcarboxy sources using a Cu(II)/TBHP catalytic system has been reported. It is a simple protocol for ortho benzoyloxylation using amides and ethers as surrogates. A broad range of amides and ethers was found to be compatible under optimized reaction conditions to provide the corresponding products in good to excellent yield. The reaction proceeds through the cleavage of C-N, C-O, and C-H bonds and the formation of a new C-O bond via C-H functionalization.
- Yedage, Subhash L.,Bhanage, Bhalchandra M.
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supporting information
p. 2161 - 2169
(2015/09/15)
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- Tunable arylative cyclization of 1,6-enynes triggered by rhodium(III)-catalyzed C-H activation
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Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an N-Michael addition process or hydrobenzofurans through a C-Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of CpRhIII-catalyzed C-H activation cascade reactions.
- Fukui, Yuki,Liu, Ping,Liu, Qiang,He, Zhi-Tao,Wu, Nuo-Yi,Tian, Ping,Lin, Guo-Qiang
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supporting information
p. 15607 - 15614
(2014/12/11)
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- A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides
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An efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides was developed. A variety of anilides reacted with aryl acylperoxides to afford the corresponding ortho-arylation products, and N-methoxyarylamides generated phenanthridinones. This journal is
- Li, Dengke,Xu, Ning,Zhang, Yicheng,Wang, Lei
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supporting information
p. 14862 - 14865
(2014/12/11)
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- Metal-free iodine(III)-promoted synthesis of isoquinolones
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A metal-free oxidative cycloaddition reaction of substituted benzamides and alkynes has been developed for the synthesis of isoquinolones by using bis(trifluoracetoxy)iodobenzene (PIFA) and trifluoroacetic acid (TFA). Under mild conditions, a wide variety of isoquinolones were conveniently prepared via oxidative annulation of simple N-methoxybenzamide and diarylacetylene or aryl/alkyl acetylene derivatives in yields up to 87%.
- Chen, Zhi-Wei,Zhu, Yi-Zhou,Ou, Jin-Wang,Wang, Ya-Ping,Zheng, Jian-Yu
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p. 10988 - 10998
(2015/01/08)
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- Mild rhodium(III)-catalyzed C-H allylation with 4-vinyl-1,3-dioxolan-2-ones: Direct and stereoselective synthesis of (E)-allylic alcohols
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A rhodium(III)-catalyzed C-H direct allylation reaction with 4-vinyl-1,3-dioxolan-2-ones has been developed. The reaction provides a facile and stereoselective access to substituted-(E)-allylic alcohols under mild and redox-neutral reaction conditions. Olefinic C-H activation is applicable, giving multifunctionalized skipped dienes in good yields. Minimal double-bond migration was observed.
- Zhang, Shang-Shi,Wu, Jia-Qiang,Lao, Ye-Xing,Liu, Xu-Ge,Liu, Yao,Lv, Wen-Xin,Tan, Dong-Hang,Zeng, Yao-Fu,Wang, Honggen
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supporting information
p. 6412 - 6415
(2015/01/09)
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- Copper-mediated direct aryloxylation of benzamides assisted by an N, O -bidentate directing group
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Copper-mediated selective mono- or diaryloxylation of benzamides has been achieved by using 2-aminopyridine 1-oxide as a new and removable N,O-bidentate directing group. The reaction system shows a broad substrate scope and provides a straightforward way for the synthesis of mono- and diaryloxylated benzoic acids.
- Hao, Xin-Qi,Chen, Li-Juan,Ren, Baozeng,Li, Liu-Yan,Yang, Xin-Yan,Gong, Jun-Fang,Niu, Jun-Long,Song, Mao-Ping
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supporting information
p. 1104 - 1107
(2014/03/21)
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- Copper-catalyzed C-N bond formation through C-H/N-H activation: A novel approach to the synthesis of multisubstituted ureas
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A copper-catalyzed cross-dehydrogenative coupling reaction that involves C-H activation of formamides and N-H activation of N-alkoxy amides has been developed. This protocol affords a novel approach to the synthesis of multisubstituted ureas under mild co
- Jiang, Honglai,Lin, Aijun,Zhu, Chengjian,Cheng, Yixiang
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supporting information
p. 819 - 821
(2013/02/23)
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- Efficient synthesis of hydroxyl isoindolones by a Pd-mediated C-H activation/annulation reaction
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Radical reaction: A convenient synthesis of hydroxyl isoindolones by a Pd-catalyzed C-H activation/annulation reaction with near "click chemistry" efficiency is presented (see scheme; TBHP=tert-butyl hydrogen peroxide). This methodology features short reaction times (10-30 min), high atom economy, wide substrate scope (22 examples), and good reaction yields (up to 93 %). Copyright
- Yu, Qingzhen,Zhang, Nana,Huang, Jianhui,Lu, Shaonan,Zhu, Yi,Yu, Xiaoxiao,Zhao, Kang
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p. 11184 - 11188
(2013/09/02)
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- Synthesis of biaryl imino/keto carboxylic acids via aryl amide directed C-H activation reaction
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A novel Pd-catalysed C-H activation reaction for the synthesis of biaryl imino/keto carboxylic acids is developed. This reaction underwent aryl amide directed C-H activation ortho-acylation followed by ring closing and ring opening processes to give a range of biaryl imino/keto carboxylic acids. Our methodology features the utilization of a cheap and green oxidant (TBHP) as well as readily available aldehydes.
- Zhang, Nana,Yu, Qingzhen,Chen, Ruixue,Huang, Jianhui,Xia, Yeqing,Zhao, Kang
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supporting information
p. 9464 - 9466
(2013/10/01)
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- Copper-catalyzed cross-coupling of O -alkyl hydroxamates with aryl iodides
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N-Aryl-O-alkylhydroxamic acid derivatives were prepared by copper-catalyzed cross-coupling of hydroxamates with aryl iodides. The reaction conditions are compatible with standard hydroxy-protecting groups on the hydroxylamine moiety and are applicable to
- Kukosha, Tatyana,Trufilkina, Nadezhda,Belyakov, Sergey,Katkevics, Martins
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supporting information; experimental part
p. 2413 - 2423
(2012/09/07)
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- Organocatalytic, oxidative, intermolecular amination and hydrazination of simple arenes at ambient temperature
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New atom-economical, environmental friendly, direct oxidative intermolecular processes of amination and hydrazination of nonprefunctionalized arenes were developed. The products were formed in a good regioselective manner under organocatalytic conditions
- Samanta, Rajarshi,Antonchick, Andrey P.,Bauer, Jonathan O.,Strohmann, Carsten
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supporting information
p. 5518 - 5521,4
(2012/12/12)
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- Rhodium(III)-catalyzed intermolecular direct amination of aromatic C-H bonds with N-chloroamines
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A Rh(III)-catalyzed direct aromatic C-H amination is achieved using N-chloroamines as a reagent. Furthermore, we also developed a one-pot amination protocol involving in situ chlorination of the secondary amines. The catalytic amination operates at mild conditions with excellent functional group tolerance and regioselectivity.
- Ng, Ka-Ho,Zhou, Zhongyuan,Yu, Wing-Yiu
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supporting information; experimental part
p. 272 - 275
(2012/02/04)
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- Synthesis and thermal decomposition of N,N-dialkoxyamides
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N,N-Dialkoxyamides 1c, a virtually unstudied member of the new class of anomeric amides, amides bearing two electronegative atoms at nitrogen, have been synthesised in useful yields directly from hydroxamic esters using phenyliodine(iii)bis(trifluoroacetate) (PIFA). Infrared carbonyl stretch frequencies and carbonyl 13C NMR properties have been reported, which support strong inhibition of amide resonance in these amides. Their thermal decomposition reactions in mesitylene at 155°C proceed by homolysis to form alkoxyamidyl and alkoxyl free radicals in preference to HERON rearrangements to esters. The reactions follow first-order kinetics and for a series of N,N-dimethoxy-4-substituted benzamides, activation energies of 125-135 kJ mol-1 have been determined together with weakly negative entropies of activation.
- Digianantonio, Katherine M.,Glover, Stephen A.,Johns, Jennifer P.,Rosser, Adam A.
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experimental part
p. 4116 - 4126
(2011/06/28)
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- New heteroannulation reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H activation
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A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from N-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Subs
- Wrigglesworth, Joe W.,Cox, Brian,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.
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supporting information; experimental part
p. 5326 - 5329
(2011/12/01)
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- One-pot formation of C-C and C-N bonds through palladium-catalyzed dual C-H activation: Synthesis of phenanthridinones
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Two cycles in one pot! The synthesis of biologically important phenanthridinones has been achieved by the one-pot formation of C-C and C-N bonds through a palladium-catalyzed dual C-H activation, which involves four bond ruptures and two bond formations (see scheme). The conversion of phenanthridinones into natural product like derivatives further demonstrates the utility of this synthetic achievement.
- Wang, Guan-Wu,Yuan, Ting-Ting,Li, Dan-Dan
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supporting information; experimental part
p. 1380 - 1383
(2011/04/18)
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- Synthesis of isoindolinones via palladium-catalyzed C-H activation of N-methoxybenzamides
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The synthesis of isoindolinones from N-methoxybenzamides and alkenes has been achieved by Pd-catalyzed ortho sp2 C-H activation and intramolecular oxidative amidation, which involve the cleavage of four bonds and formation of two bonds.
- Li, Dan-Dan,Yuan, Ting-Ting,Wang, Guan-Wu
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supporting information; experimental part
p. 12789 - 12791
(2012/01/05)
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- Magnetic glyco-nanoparticles: A tool to detect, differentiate, and unlock the glyco-codes of cancer via magnetic resonance imaging
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Within cancer, there is a large wealth of diversity, complexity, and information that nature has engineered rendering it challenging to identify reliable detection methods. Therefore, the development of simple and effective techniques to delineate the fin
- Ei-Boubbou, Kheireddine,Zhu, David C.,Vasileiou, Chrysoula,Borhan, Babak,Prospen, Davide,Wei,Huang, Xuefei
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supporting information; scheme or table
p. 4490 - 4499
(2010/06/13)
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- N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with O-acetyl hydroxamic acids
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(Chemical Equation Presented) A general nonoxidative N-amidation of organostannanes and boronic acids has been developed. Under nonbasic conditions a wide variety of aryl, alkenyl, and heteroaryl organostannanes and boronic acids couple efficiently with O-acetyl hydroxamic acids in the presence of Cu(I) sources.
- Zhang, Zhihui,Yu, Ying,Liebeskind, Lanny S.
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supporting information; experimental part
p. 3005 - 3008
(2009/04/18)
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- Photochemistry of sulfilimine-based nitrene precursors: Generation of both singlet and triplet benzoylnitrene
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(Graph Presented) Photolysis of N-benzoyl-S,S-diphenylsulfilimine or N-benzoyl dibenzothiophene sulfilimine produces PhNCO and also benzoylnitrene. Direct observation of the triplet nitrene, energetic differences between the singlet and triplet state of the nitrene, and oxygen quenching experiments suggest that the triplet nitrene derives from the triplet excited state of the sulfilimine precursors, rather than through equilibration of nearby singlet and triplet states of the nitrene itself. In acetonitrile, the formation of an ylide, followed by cyclization to the corresponding oxadiazole, is the predominant nitrene chemistry, occurring on the time scale of a few microseconds and few tens of microseconds, respectively. Trapping experiments with substrates such as cis-4-octene suggest that reactivity of the nitrene is mainly through the singlet channel, despite a fairly small energy gap between the singlet ground state and the triplet.
- Desikan, Vasumathi,Liu, Yonglin,Toscano, John P.,Jenks, William S.
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p. 6848 - 6859
(2008/02/11)
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- Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone
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The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone.
- Miyata, Okiko,Koizumi, Tomoko,Asai, Hiroshi,Iba, Ryuichi,Naito, Takeaki
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p. 3893 - 3914
(2007/10/03)
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