- Regio- and Stereoselective N-addition to an Open Bromo Vinyl Cation
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A protocol for the synthesis of thus far inaccessible bromo vinyl triflimides is presented. Our previously reported concept of assisted vinyl cation formation was engaged to achieve both a protonation of relatively electron poor bromo alkynes and a reaction with high regio- and stereoselectivity. To the best of our knowledge, this is the first stereoselective addition of an N-nucleophile to an open β-halovinyl cation.
- Chuchmareva, Marina,Collong, Arndt,Niggemann, Meike,Schr?der, Sebastian,Strauch, Christina
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supporting information
(2021/06/07)
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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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- A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes
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We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).
- Chen, Ping,Cao, Wei,Li, Xiangqian,Shi, Dayong
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supporting information
p. 4789 - 4794
(2021/09/02)
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- Direct oxidation ofN-ynylsulfonamides intoN-sulfonyloxoacetamides with DMSO as a nucleophilic oxidant
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N-Arylethynylsulfonamides are oxidized intoN-sulfonyl-2-aryloxoacetamides directly and efficiently with dimethyl sulfoxide (DMSO) as both an oxidant and solvent with microwave assistance. DFT calculations indicate that DMSO nucleophilically attacks the ethylic triple bond and transfers its oxygen atom to the triple bond to form zwitterionic anionicN-sulfonyliminiums to trigger the reaction. Then it nucleophilically attacks the generated iminium intermediates to accomplish the oxidationviathe second oxygen atom transfer. The current method provides a straightforward and efficient strategy to transform variousN-arylethynylsulfonamides intoN-sulfonyl-2-aryloxoacetamides, sulfonyl oxoacetimides, without any other electrophilic activators or oxidants.
- Dong, Jun,Fu, Duo,Sheng, Dongning,Wang, Jiayi,Xu, Jiaxi
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p. 40243 - 40252
(2021/12/31)
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- DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes
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Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).
- Thummala, Yadagiri,Karunakar, Galla V.,Doddi, Venkata Ramana
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supporting information
p. 611 - 616
(2019/01/04)
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- Monobrominated alkyne compound, preparation method and application thereof
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The invention belongs to the technical field of synthetic chemistry and discloses a monobrominated alkyne compound, a preparation method and an application thereof. The chemical structure formula of the monobrominated alkyne compound is as follows, wherei
- -
-
Paragraph 0046; 0047; 0048
(2019/02/04)
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- Gold-Catalyzed C(sp2)?C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes
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A gold(I)-catalyzed cascade cyclization–alkynylation of allenoates using alkynyl bromide to generate β-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of β-alkynyl-γ-butenolides in moderate to good yields without the need for any external oxidant.
- Yang, Yangyang,Schie?l, Jasmin,Zallouz, Sirine,G?ker, Verena,Gross, Jürgen,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 9624 - 9628
(2019/07/05)
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- Gold Catalyzed Photoredox C1-Alkynylation of N-Alkyl-1,2,3,4- tetrahydroisoquinolines by 1-Bromoalkynes with UVA LED Light
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A synthetic method that combines [Au2(m-dppm)2]Cl2 (dppm=bis(diphenylphosphanyl)methane) and UVA LED (LED=light emitting diode) light (365 nm) to catalyze the regioselective C1-alkynylation of N-alkyl-1,2,3,4-tetrahydroisoquinolines (THIQs) with alkynyl bromides is described. The reaction mechanism was delineated to involve a reductive quench pathway to generate the two posited radical species of the nitrogen-containing heterocycle and organic halide. In contrast, radical formation via an oxidative quench pathway was suggested to be operative in analogous control experiments with a 1-iodoalkyne. The usefulness of this carbon-carbon bond forming strategy was also exemplified by its application to the formal synthesis of the opioid analgesic drug methopholine and synthesis of a protoberberine alkaloid derivative.
- Zhao, Yichao,Jin, Jianwen,Chan, Philip Wai Hong
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supporting information
p. 1313 - 1321
(2019/06/03)
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- A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water
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Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.
- Yang, Yunqin,Meng, Xiangtai,Zhu, Baolong,Jia, Ying,Cao, Xiaoji,Huang, Shenlin
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supporting information
p. 1166 - 1169
(2019/01/04)
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- Copper-catalyzed one-pot synthesis of alkynylphophonates
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Copper is found to be an effective catalyst for the preparation of alkynylphophonates. A novel copper-catalyzed one-pot synthesis of alkynylphophonates from terminal alkynes and dialkyl phosphites is developed which involves the haloalkynes intermediates. This method provides a unique and alternative approach to the well-documented oxidative coupling or arylpropiolic acid strategies.
- Song, Wang-Ze,Li, Jun-Hao,Li, Ming,He, Jun-Nan,Dong, Kun,Ullah, Karim,Zheng, Yu-Bin
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supporting information
p. 697 - 703
(2019/02/16)
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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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- TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids
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A rapid process for decarboxylative bromination of α,β-unsaturated carboxylic acids have been developed using N,N-dibromo-p-toluenesulfonamide (TsNBr2). Treatment of cinnamic acids with TsNBr2 in presence of potassium carbonate in acetonitrile produces corresponding β-bromostyrenes at room temperature. Exclusive formation of (E)-β-bromostyrenes was observed in a stereoselective manner within a very short period of time (5–15 min). This method was further extended for obtaining 1-bromoalkynes from corresponding propiolic acids. Instantaneous formation of bromoalkynes was observed when the reaction was carried out in presence of DBU as a base in acetonitrile at room temperature. A wide variety of cinnamic acids and propiolic acids could be converted to corresponding β-bromostyrenes and 1-bromoalkynes respectively under mild reaction condition with high to excellent yield.
- Hazarika, Debojit,Phukan, Prodeep
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supporting information
p. 4593 - 4596
(2018/11/23)
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- Gold-Catalyzed Intermolecular [4+2] Annulation of 2-Ethynylanilines with Ynamides: An Access to Substituted 2-Aminoquinolines
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A gold-catalyzed intermolecular [4+2] annulation of easily accessible 2-ethynylanilines with ynamides offers a highly region-selective, modular, efficient, and atom-economical strategy for the synthesis of substituted 2-aminoquinolines in up to 93% yield. (Figure presented.).
- Zhao, Ximei,Song, Xinlong,Jin, Hongming,Zeng, Zhongyi,Wang, Qian,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 2720 - 2726
(2018/07/29)
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- Photochemical Dual-Catalytic Synthesis of Alkynyl Sulfides
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A photochemical dual-catalytic cross-coupling to form alkynyl sulfides via C(sp)?S bond formation is described. The cross-coupling of thiols and bromoalkynes is promoted by a soluble organic carbazole-based photocatalyst using continuous flow techniques. Synthesis of alkynyl sulfides bearing a wide range of electronically and sterically diverse aromatic alkynes and thiols can be achieved in good to excellent yields (50–96 %). The simple continuous flow setup also allows for short reaction times (30 min) and high reproducibility on gram scale. In addition, we report the first application of photoredox/nickel dual catalysis towards macrocyclization, as well as the first example of the incorporation of an alkynyl sulfide functional group into a macrocyclic scaffold.
- Santandrea, Jeffrey,Minozzi, Clémentine,Cruché, Corentin,Collins, Shawn K.
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p. 12255 - 12259
(2017/09/06)
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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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- Highly efficient and recyclable catalyst for the direct chlorination, bromination and iodination of terminal alkynes
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Direct halogenation, including chlorination, bromination and iodination of terminal alkynes, are of great importance in organic synthesis. Here an efficient and recyclable nano-Ag/g-C3N4 catalyst system was developed and proved to be remarkably active with 39 examples varied from chlorination, bromination to iodination, of which 14 runs have yielded more than 95% of the product. Recycling of the catalyst was also achieved without obvious activity loss after several runs: 99% yield was observed even after 5 runs in the bromination of phenylacetylene. The catalysts system is of low cost and easy to be prepared, making this procedure versatile, convenient and economic.
- Shi, Wei,Guan, Zhipeng,Cai, Peng,Chen, Hao
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p. 199 - 204
(2017/08/10)
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- α-Imino Gold Carbenes from 1,2,4-Oxadiazoles: Atom-Economical Access to Fully Substituted 4-Aminoimidazoles
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A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access α-imino gold carbenes, which corresponds to an unprecedented intermolecular transfer of N-acylimino nitrenes to ynamides. Moreover, the reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale.
- Zeng, Zhongyi,Jin, Hongming,Xie, Jin,Tian, Bing,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 1020 - 1023
(2017/03/15)
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- Regioselective TfOH-mediated hydroamidation of ynamides with nitriles
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A new TfOH-mediated reaction of ynamides with nitriles as nucleophiles has been developed. The reaction works efficiently under mild reaction conditions to afford a new class of α-acylaminoenamides readily via the intermediacy of keteniminium ion. The reaction displays generality and a broad substrates scope. Additionally, the α-acylaminoenamides could be transformed to highly substituted pyridine, 4-aminopyrimidine or isoquinoline cores.
- Wang, Wan-Shu,Chen, Ping,Tang, Yu
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p. 2731 - 2739
(2017/04/14)
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- TsNBr2mediated oxidative functionalization of alkynes
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A new approach has been developed for oxidative transformation of alkynes by controlled manipulation of TsNBr2mediated process. Alkynes could be readily converted to ketones and α-bromoketones via an oxybromination–debromination sequence. When alkynes are treated successively with TsNBr2, KI and Na2SO3in a mixture of acetone and water at room temperature, corresponding ketones were obtained. On the other hand, treatment of alkynes with TsNBr2and Na2SO3in a mixture of ethyl acetate, acetone and water at room temperature could produce corresponding α-bromoketones. 1-Bromoalkynes could also be synthesized from corresponding alkynes within a very short time using TsNBr2at room temperature. In all cases, excellent yields of corresponding products are obtained.
- Rajbongshi, Kamal Krishna,Hazarika, Debojit,Phukan, Prodeep
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p. 4151 - 4158
(2016/07/06)
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- First Catalyzed Hydration of Haloalkynes by a Recyclable Catalytic System
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The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also be scaled up.
- Zou, Huaxu,He, Weibao,Dong, Qizhi,Wang, Ruijia,Yi, Niannian,Jiang, Jun,Pen, Dongming,He, Weimin
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p. 116 - 121
(2016/01/26)
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- Copper(I)-Catalyzed Three-Component Click/Alkynylation: One-Pot Synthesis of 5-Alkynyl-1,2,3-triazoles
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A copper(I)-catalyzed tandem CuAAC/alkynylation reaction of various alkynes, organic azides, and bromoalkynes to provide rapid access to 5-alkynyl-1,2,3-triazoles has been developed. The reaction proceeded via a copper-catalyzed alkyne azide cycloaddition
- Wang, Weiguo,Wei, Fang,Ma, Yudao,Tung, Chen-Ho,Xu, Zhenghu
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supporting information
p. 4158 - 4161
(2016/10/11)
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- Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides to yield 1-amino-1H-indenes
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Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides yield 1-amino-1H-indenes in two distinct pathways; the success of these annulations relies on the high electrophilicity of α-cyano arylgold carbenes to activate an ionic pathway.
- Singh, Rahulkumar Rajmani,Pawar, Samir Kundlik,Huang, Min-Jie,Liu, Rai-Shung
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supporting information
p. 11434 - 11437
(2016/09/23)
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- An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin
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An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.
- Liu, Shihui,Chen, Xiaobei,Hu, Yanwei,Yuan, Laiqi,Chen, Shaohua,Wu, Ping,Wang, Wei,Zhang, Shilei,Zhang, Wei
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p. 553 - 560
(2015/03/05)
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- Rapid access to unsymmetrical 1,3-diynes and 2,5-disubstituted thiophenes under ligand and Pd/Ni-free Cu-catalysis
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A Pd/Ni-free copper-catalysed tandem synthesis was realized for rapid access to unsymmetrical 1,3-diynes from 1,1-dibromoalkenes and terminal alkynes. This method was extended to the straightforward synthesis of unsymmetrical 2,5-disubstituted thiophenes
- Rao, Maddali L. N.,Islam, Sk Shamim,Dasgupta, Priyabrata
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p. 78090 - 78098
(2015/09/28)
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- Regioselective Synthesis of Polyheterohalogenated Naphthalenes via the Benzannulation of Haloalkynes
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Independent control of halide substitution at six of the seven naphthalene positions of 2-arylnaphthalenes is achieved through the regioselective benzannulation of chloro-, bromo-, and iodoalkynes. The modularity of this approach is demonstrated through the preparation of 44 polyheterohalogenated naphthalene products, most of which are difficult to access through known naphthalene syntheses. The outstanding regioselectivity of the reaction is both predictable and proven unambiguously by single-crystal X-ray diffraction for many examples. This synthetic method enables the rapid preparation of complex aromatic systems poised for further derivatization using established cross-coupling methods. The power and versatility of this approach makes substituted naphthalenes highly attractive building blocks for new organic materials and diversity-oriented synthesis.
- Lehnherr, Dan,Alzola, Joaquin M.,Lobkovsky, Emil B.,Dichtel, William R.
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supporting information
p. 18122 - 18127
(2015/12/24)
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- Cobalt(II)-catalyzed electrophilic alkynylation of 1,3-dicarbonyl compounds to form polysubstituted furans via π-π Activation
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Polysubstituted furans were obtained with excellent yields via the electrophilic alkynylation of 1,3-dicarbonyl compoundsws with phenyl- or ester-substituted brominated alkynes. The reaction is catalyzed by the inexpensive and readily available catalyst, cobalt(II) chloride, and has a wide substrate scope. The C(sp)-C(sp3) coupling occurs under mild conditions with short reaction times and does not require an inert atmosphere or ligands. It is proposed that the reaction proceeds through a chelation complex of cobalt(II) with the deprotonated 1,3-dicarbonyl compound.
- Roslan, Irwan Iskandar,Sun, Jiulong,Chuah, Gaik-Khuan,Jaenicke, Stephan
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supporting information
p. 719 - 726
(2015/03/18)
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- Copper-catalyzed N-alkynylations of sulfoximines with bromoacetylenes
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N-Alkynylated sulfoximines have been obtained by copper-catalyzed cross-coupling reactions starting from NH-sulfoximines and bromoacetylenes in moderate to good yields. The reaction conditions are mild, and the substrate scope is wide.
- Chen, Xiao Yun,Wang, Long,Frings, Marcus,Bolm, Carsten
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p. 3796 - 3799
(2014/08/05)
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- Copper-catalyzed cross-coupling of vinylsiloxanes with bromoalkynes: Synthesis of enynes
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Enynes are versatile building blocks in organic synthesis. A copper-catalyzed Hiyama-type cross-coupling of vinylsiloxanes with bromoalkynes is presented. This mild and efficient method led to the formation of various sensitive enynes. The use of cis, trans, and 1,1′-disubstituted vinylsiloxanes was allowed, and full retention of stereochemistry was observed. Sensitive groups such as halides, unsaturated ketones, and aldehydes were fully tolerated.
- Cornelissen, Loic,Lefrancq, Maxime,Riant, Olivier
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supporting information
p. 3024 - 3027
(2014/06/23)
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- Copper catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts
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Cu-catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts with alkynyl bromides and alkynyl chlorides is described. This new reaction can be used for preparing functionalized butynenitrile derivatives.
- Feng, Yi-Si,Xu, Zhong-Qiu,Mao, Long,Zhang, Feng-Feng,Xu, Hua-Jian
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p. 1472 - 1475
(2013/06/27)
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- Palladium-catalyzed alkynylative lactonization of unsaturated bicyclic carboxylic acids: Synthesis of fused polycyclic γ-lactone compounds
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Unsaturated bicyclic carboxylic acids undergo palladium-catalyzed coupling with bromoalkynes to produce γ-alkynyl lactones in moderate to good yields with excellent chemo- and regioselectivity. The reaction conditions were extremely mild, and functional groups such as methyl, methoxy, chloro, and bromo were tolerated under the optimized reaction conditions. Moreover, γ-chloroalkenyl lactones were facilely synthesized through chloropalladation/carboesterification of electron-deficient C≡C bonds by using molecular oxygen as the sole oxidant. Facile and tandem Pd-catalyzed synthesis of γ-alkynyl lactone and γ-chloroalkenyl lactone derivatives by using readily accessible bromoalkynes and unsaturated bicyclic carboxylic acids is reported. Two subsequent steps, namely, C(sp or sp 2)-C(sp3) bond formation and C-O bond formation, are catalyzed by a single Pd catalyst. The reactions proceed with good yields of the products. Copyright
- Sun, Ning,Li, Yibiao,Yin, Gengming,Jiang, Shaohua
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supporting information
p. 2541 - 2544
(2013/06/04)
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- Gold-catalyzed hydration of haloalkynes to α-halomethyl ketones
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A general atom-economical approach for the synthesis of α-halomethyl ketones is demonstrated through hydration of a wide range of haloalkynes. Other outstanding features include excellent yields from both alkyl- and aryl-substituted haloalkynes and wide functional group tolerance. This protocol is an alternative to conventional α-halogenation of ketones.
- Xie, Longyong,Wu, Yundong,Yi, Weiguo,Zhu, Lei,Xiang, Jiannan,He, Weimin
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p. 9190 - 9195
(2013/10/08)
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- Pd-catalyzed and CsF-promoted reaction of bromoalkynes with isocyanides: Regioselective synthesis of substituted 5-iminopyrrolones
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The palladium-catalyzed and CsF-promoted annulation reaction of bromoalkynes and isocyanides regioselectively affords a diverse set of 5-iminopyrrolone derivatives. This chemistry presumably proceeds through the bromoacrylamide intermediates, which can be readily prepared from the nucleophilic addition reaction of isocyanides to bromoalkynes in the presence of CsF.
- Li, Yibiao,Zhao, Jian,Chen, Huoji,Liu, Bifu,Jiang, Huanfeng
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supporting information; experimental part
p. 3545 - 3547
(2012/06/01)
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- Synthesis of heteroaryl ketones via tandem reaction of 1,1-dibromoethenes
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A novel method for the synthesis of heteroaryl ketones through one-pot tandem reaction of 1,1-dibromoethenes with 2-amino(thio)phenols promoted by TBAF·3H2O and RuCl3(5%)/air was developed. This novel method includes several reactions in one-pot and utilizes economical yet efficient reagents to generate synthetically and biologically interesting heteroaryl ketones under mild conditions with good efficiency.
- Fan, Xuesen,He, Yan,Zhang, Xinying,Guo, Shenghai,Wang, Yangyang
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experimental part
p. 6369 - 6374
(2011/09/12)
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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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- Expedient synthesis of functionalized conjugated enynes: Palladium-catalyzed bromoalkynylation of alkynes
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(Chemical Equation Presented) Side by side: Direct cis addition of bro-moalkynes 1 to various alkynes 2 was found to proceed in the presence of a PdII catalyst to give difunctionalized enyne products 3. The method is facile for the synthesis of bromo alkenynes. Further-more, an unusual mechanism is pro-posed.
- Li, Yibiao,Liu, Xiaohang,Jiang, Huanfeng,Feng, Zhenning
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supporting information; experimental part
p. 3338 - 3341
(2010/07/10)
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- Highly efficient two-step synthesis of (Z)-2-halo-1-iodoalkenes from terminal alkynes
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The easily accessible haloalkynes can be converted to (Z)-2-halo-1- iodoalkenes in high yields with excellent regio- and stereoselectivity. The method shows good functional group compatibility. The resulting products could find broad applications.
- Chen, Zhengwang,Jiang, Huanfeng,Li, Yibiao,Qi, Chaorong
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supporting information; experimental part
p. 8049 - 8051
(2011/01/03)
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- DBU/DMSO Promoted Dehydrobromination of 1,1-Dibromoolefins. A General Synthesis of 1-Bromoaromatic Alkynes under mild Conditions
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A new procedure for the synthesis of 1-bromoalkynes by DMSO/DBU induced dehydrobromination of 1,1-dibromoethylenes under mild conditions is described.
- Ratovelomanana, Victorin,Rollin, Yolande,Gebehenne, Catherine,Gosmini, Corinne,Perichon, Jacques
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p. 4777 - 4780
(2007/10/02)
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- SYNTHESIS AND DEHYDROBROMINATION OF 2,2,2-TRIBROMO-1-ARYLETHANES
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The synthesis of 2,2,2-tribromo-1-arylethanes by the alkylation of tribromomethyl anion with the corresponding arylbromomethanes is described.Conditions were determined for the transformation of the tribromides into 2,2-dibromo-1-arylethenes and bromo(aryl)ethynes.
- Kostikov, R. R.,Krasikov, A. Ya.,Mandel'shtam, T. V.,Kharicheva, E. M.
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p. 294 - 298
(2007/10/02)
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