- Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids
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A visible-light-promoted oxo-sulfonylation of ynamides with sulfonic acids is reported, giving rise to a collection of functionalized α-sulfonylated amides in a straightforward manner. The reaction proceeds sequentially through a cascade of electrophilic addition and photoinduced sulfonyl radical-sustained skeleton rearrangement. The high atom economy, mild reaction conditions, and wide substrate scope comprised the merits of this synthetic transformation.
- Wang, Lu,Lu, Chengrong,Yue, Yanni,Feng, Chao
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- Visible-Light-Promoted Formation of C—C and C—P Bonds Derived from Evolution of Bromoalkynes under Additive-Free Conditions: Synthesis of 1,1-Dibromo-1-en-3-ynes and Alkynylphosphine Oxides
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The controllable achievement of C—C and C—P bond formations is developed via visible-light-promoted bromoalkyne dimerization or its further transformation with secondary phosphine oxides. The 1,1-dibromo-1-en-3-ynes are formed when bromoalkyne is exposed to visible-light. While alkynylphosphine oxides are generated when bromoalkynes are mixed with secondary phosphine oxides.
- Xu, Hailong,Chen, Rui,Ruan, Hongjie,Ye, Ruyi,Meng, Ling-Guo
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supporting information
p. 873 - 878
(2021/03/04)
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- Palladium-Catalyzed Carbonylation in the Synthesis of N-Ynonylsulfoximines
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Palladium-catalyzed carbonylation reactions with Cr(CO)6 as carbonyl source are key for the preparation of N-ynonylsulfoximines from NH-sulfoximines and bromoalkynes. The couplings proceed at room temperature with a wide range of substrate combinations affording the corresponding products in good yields. (Figure presented.).
- Ma, Ding,Wang, Chenyang,Kong, Deshen,Tu, Yongliang,Shi, Peng,Bolm, Carsten
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supporting information
p. 1330 - 1334
(2021/01/26)
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- Catalytic Synthesis of Dibenzazepines and Dibenzazocines by 7-Exo- and 8-Endo-Dig-Selective Cycloisomerization
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The 7-exo- and 8-endo-dig-selective gold-catalyzed cycloisomerizations of 2-propargylamino biphenyl derivatives were developed. The reaction of terminal alkynes gave dibenzo[b,d]azepines by 7-exo-dig cycloisomerization. In contrast, when internal alkynes were subjected to the reaction, 8-endo-dig cycloisomerization proceeded to provide dibenzo[b,d]azocines. The nucleophilicity at the reaction site and the electron-withdrawing effect of a tosyl group were important for the present selective transformation. This protocol could be used for ynamide substrates and a silver-catalyzed reaction gave 7-exo-dig products selectively.
- Ito, Mamoru,Takaki, Asahi,Okamura, Moeka,Kanyiva, Kyalo Stephen,Shibata, Takanori
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supporting information
p. 1688 - 1692
(2021/03/22)
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- A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization
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Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.
- Li, Sifan,Wang, Yu,Wu, Zibo,Shi, Weiliang,Lei, Yibo,Davies, Paul W.,Shu, Wei
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p. 7209 - 7214
(2021/09/14)
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- Alpha-aminoamide derivative and application thereof
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The invention discloses an alpha-amino amide derivative and applications thereof, and particularly relates to a class of novel alpha-amino amide derivatives and a pharmaceutical composition containingthe compound. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and applications of the compound and the pharmaceutical composition in preparationof drugs for treating diseases regulated by MAO-B inhibitors, including neurodegenerative diseases, especially Parkinson's disease.
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Paragraph 0226-0230
(2020/05/14)
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- Visible Light-Induced Difunctionalization of Alkynes: The Synthesis of Thiazoles and 1,1-Dibromo-1-en-3-ynes
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A visible light-induced cascade cyclization of thioamides with alkynes was developed to synthesize 1,3-thiozoles. The sulfur radical generated from thioamide via the single-electron transfer (SET) pathway was promoted by photocatalysis as a key intermediate in this reaction. When bromoalkynes were used as the substrate, the self-coupling products 1,1-dibromo-1-en-3-ynes were obtained in moderate yields, and an energy transfer pathway for this transformation promoted by visible-light photocatalysis was proposed.
- Huang, Xiaoying,Chen, Hui,Huang, Zhongzhi,Xu, Yanli,Li, Fangyao,Ma, Xianli,Chen, Yanyan
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p. 15283 - 15293
(2019/12/04)
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- Palladium-Catalyzed Oxygenative Cross-Coupling of Ynamides and Benzyl Bromides by Carbene Migratory Insertion
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A palladium-catalyzed oxygenative cross-coupling of ynamides and benzyl bromides has been developed. After subsequent hydrogenation, α,α-disubstituted amide derivatives were obtained in good yields. Migratory insertion of α-oxo palladium carbene species, generated by intermolecular oxidation, is proposed as the key step in this reaction. The study demonstrates the potential of ynamides to serve as carbene precursors in palladium-catalyzed C?C bond-forming cross-coupling reactions.
- Gao, Yunpeng,Wu, Guojiao,Zhou, Qi,Wang, Jianbo
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supporting information
p. 2716 - 2720
(2018/02/13)
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- Dual Gold-Catalyzed Formal Tetradehydro-Diels–Alder Reactions for the Synthesis of Carbazoles and Indolines
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This work reports a dual gold-catalyzed tetradehydro-Diels–Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels–Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 π electrocyclization, followed with 1,2-hydrogen shift.
- Wang, Hong-Fa,Wang, Shi-Yue,Qin, Tian-Zhu,Zi, Weiwei
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supporting information
p. 17911 - 17914
(2018/11/23)
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- Controlled Reactivity of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Selective Synthesis of 1-(Bromoethynyl)arenes
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The nucleophilic reactivity of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was completely controlled by the formation of monohydrate (DBU?H2O) in the synthesis of 1-(bromoethynyl)arenes from 1,1-dibromoalkenes. Differential reactivity of DBU in pr
- Krishna Moodapelly, Shiva,Sharma, Gangavaram V. M.,Ramana Doddi, Venkata
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supporting information
p. 1535 - 1540
(2017/05/05)
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- Regioselective Synthesis of 5-Aminooxazoles via Cp?Co(III)-Catalyzed Formal [3 + 2] Cycloaddition of N-(Pivaloyloxy)amides with Ynamides
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A simple and efficient protocol for the regioselective synthesis of 5-aminooxazoles is disclosed. The reaction, catalyzed by a cheap Cp?Co(III) catalyst, starts from easily accessible N-(pivaloyloxy)amides and ynamides. Mild reaction conditions, a broad s
- Han, Xiang-Lei,Zhou, Chu-Jun,Liu, Xu-Ge,Zhang, Shang-Shi,Wang, Honggen,Li, Qingjiang
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supporting information
p. 6108 - 6111
(2017/11/27)
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- Palladium-catalyzed bromoalkynylation of C-C double bonds: Ring-structure-dependent synthesis of 7-alkynyl norbornanes and cyclobutenyl halides
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Strain versus flexibility: The palladium-catalyzed reaction of haloalkynes with norbornene derivatives leads to 7-alkynyl norbornane products (see scheme). Key to the success of this reaction is the formation of a "bridging" palladium species, which can rearrange to result in a C-7 functionalization. The ring-structure-dependent [2+2] cycloaddition of haloalkynes with cyclooctene has been achieved in moderate to good yields under similar conditions. Copyright
- Li, Yibiao,Liu, Xiaohang,Jiang, Huanfeng,Liu, Bifu,Chen, Zhengwang,Zhou, Peng
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supporting information; experimental part
p. 6341 - 6345
(2011/09/13)
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- Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols
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A novel type of carbon dioxide-mediated reaction of diyne alcohols without any metal catalysts was reported. Carbon dioxide held the key to the success of this reaction, in which 3(2H)-furanones were selectively obtained in moderate to high yields.
- Yuan, Gaoqing,He, Zaijun,Zheng, Junhua,Chen, Zhengwang,Huang, Huawen,Shi, Dabin,Qi, Chaorong,Jiang, Huanfeng
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supporting information; experimental part
p. 5956 - 5959
(2011/11/28)
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- Alkynyl halides in ruthenium(II)-catalyzed [2+2] cycloadditions of bicyclic alkenes
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Ru-catalyzed [2+2] cycloadditions between bicyclic alkenes and alkynyl halides were found to occur in moderate to good yields. The presence of the halide moiety greatly enhances the reactivity of the alkyne component in the cycloaddition and can be transformed into a variety of products that are difficult or impossible to obtain by direct cycloaddition. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Allen, Anna,Villeneuve, Karine,Cockburn, Neil,Fatila, Elisabeth,Riddell, Nicole,Tam, William
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experimental part
p. 4178 - 4192
(2009/05/27)
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- Ruthenium-catalyzed [2 + 2] cycloadditions between bicyclic alkenes and alkynyl halides
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(Chemical equation presented) Ru-catalyzed [2 + 2] cycloadditions between norbornadiene and alkynyl halides were found to occur in moderate to good yields (32-89%). The presence of the halide moiety greatly enhances the reactivity of the alkyne component in the cycloaddition and can be transformed into a variety of products that are difficult or impossible to obtain via direct cycloaddition.
- Villeneuve, Karine,Riddell, Nicole,Jordan, Robert W.,Tsui, Gavin C.,Tam, William
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p. 4543 - 4546
(2007/10/03)
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