共查询到20条相似文献,搜索用时 11 毫秒
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X Huang B Peng M Luparia LF Gomes LF Veiros N Maulide 《Angewandte Chemie (International ed. in English)》2012,51(35):8886-8890
A golden switch: Doubly stabilized sulfonium ylides can be coupled with alkynes in a gold-catalyzed synthesis of heterocycles. This method hinges on a switch in the reactivity of the sulfur ylide resulting from the simple modification of the electron-withdrawing moieties and leads to either furans or furanones bearing a quaternary center. 相似文献
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Dr. Qing‐Qing Cheng Lynée A. Massey Brook S. Willett Dr. Yongming Deng Dr. Hadi Arman Prof. Dr. Michael P. Doyle 《Angewandte Chemie (International ed. in English)》2018,57(32):10343-10346
Enoldiazoimides, a new subclass of enoldiazo compounds, generate enol‐substituted carbonyl ylides whose reactions with sulfur ylides enable an unprecedented formal [4+2] cycloaddition. The resulting multifunctionalized indolizidinones, which incorporate sulfur, are formed in good yields under mild reaction conditions. The uniqueness of this transformation stems from the role of the silyl‐protected enol, since the corresponding acetyldiazoimide failed to provide any cross‐products in metal‐catalyzed reactions with sulfur ylides. This copper‐catalyzed cycloaddition is initiated with the generation of enol‐substituted carbonyl ylides and sulfur ylides from enoldiazoimides and sulfonium salts, respectively, and proceeds through stepwise six‐membered ring formation, C?O and C?S bond cleavage, and silyl and acetyl group migration. 相似文献
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Gold‐Catalyzed Cycloisomerization of Yne‐Vinylidenecyclopropanes: A Three‐Carbon Synthon for [3+2] Cycloadditions 下载免费PDF全文
Wei Yuan Xiangying Tang Yin Wei Min Shi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(11):3198-3204
A novel type of yne‐vinylidenecyclopropanes (VDCPs) has been synthesized and applied in gold‐catalyzed cycloisomerization reactions. It was found that these compounds can undergo an intramolecular cycloisomerization and perform as a three‐carbon synthon for [3+2] cycloaddition under gold catalysis to give fused [4.3.0] and [5.3.0] bicyclic derivatives and VDCP rearranged products in moderated to good yields under mild conditions. The substrate scope of these novel transformations has been explored and plausible reaction mechanisms have been presented on the basis of deuterium labeling experiments and DFT calculations. 相似文献
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Dr. Liang‐Qiu Lu Dr. Fang Li Jing An Ying Cheng Dr. Jia‐Rong Chen Prof. Dr. Wen‐Jing Xiao 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(13):4073-4079
A hydrogen‐bond‐mediated asymmetric [4+1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins was developed. This reaction provides a facile route to enantioenriched 4,5‐substituted oxazolidinones in moderate to excellent isolated yields (65–96 %) with excellent stereocontrol (up to more than 95:5 d.r. and 97:3 e.r.). This methodology was successfully applied to the concise synthesis of two bioactive molecules. The stereocontrolled modes and mechanism have been proposed to explain the origin of this stereochemistry. 相似文献
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Jiantao Zhang Zhehui Liao Dr. Lianfen Chen Prof. Dr. Shifa Zhu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(40):9405-9409
A gold (I)-catalyzed reaction of enyne-ethers to rapidly construct oxa-bridged compounds via a tandem 1,2-acyloxy migration/intramolecular oxonium formation/1,2-rearrangement process was reported. The reaction was shown to be robust with a wide range of substitution patterns tolerated to provide the corresponding oxygen-containing bridged products in good to excellent yields. 相似文献
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Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes 下载免费PDF全文
Yuanming Li Dr. Christian Mück‐Lichtenfeld Prof. Dr. Armido Studer 《Angewandte Chemie (International ed. in English)》2016,55(46):14435-14438
The reaction of in situ generated arynes with vinyl sulfides provides benzannulated sulfonium ylides in a (3+2) cycloaddition. Trapping of the intermediate ylides with electrophiles (proton transfer or a second aryne addition) and subsequent β‐elimination give rise to di‐, tri‐, or tetrasubstituted alkenes with high stereoselectivity. Experimental studies and DFT calculations provide insight into the mechanisms of these cascade reactions. 相似文献
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Pan-Pan Gao Dong-Mei Yan Ming-Hang Bi Prof. Min Jiang Prof. Wen-Jing Xiao Prof. Jia-Rong Chen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(57):14195-14201
A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process. 相似文献
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Lothar Weber 《Angewandte Chemie (International ed. in English)》1983,22(7):516-528
In recent years both acyclic and cyclic sulfur ylides have proved to be interesting and versatile ligands in preparative organometallic chemistry. In addition to paralleling the coordination chemistry of their phosphorus analogues, sulfur ylide complexes show specific structural and chemical features; they are becoming more important in preparative inorganic and organic chemistry, and may also be biochemically relevant as methylene transfer agents. Recent studies of the complexes of the ylidic λ4-thiabenzenes and λ6-thiabenzene 1-oxides have frequently demonstrated unexpected and novel reactions, and thereby enriched the chemistry both of ylides and of carbonylmetals. 相似文献
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Hans Jürgen Bestmann 《Angewandte Chemie (International ed. in English)》1977,16(6):349-364
Phosphacumulene ylides and phosphaallene ylides are nucleophilic compounds which can add reactants in a variety of ways. Cycloadditions can occur both at the polar C—P ylide bond and at the C?C double bond. 相似文献
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Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant 下载免费PDF全文
Dr. Jin Wang Shuyao Zhang Chang Xu Dr. Lukasz Wojtas Dr. Novruz G. Akhmedov Prof. Dr. Hao Chen Prof. Dr. Xiaodong Shi 《Angewandte Chemie (International ed. in English)》2018,57(23):6915-6920
Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 % catalyst loading, up to 99 % yield) and broad substrate scope (various alkynes, inter‐ and intramolecular fashion). The gold(I) catalyst acts as both a π‐acid for alkyne activation and a redox catalyst for AuI/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant. 相似文献
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Yuan He Jiang Lou Prof. Dr. Zhengkun Yu Prof. Dr. Yong-Gui Zhou 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(22):4941-4946
Concise construction of furan and thiophene units has played an important role in the synthesis of potentially bioactive compounds and functional materials. Herein, an efficient Lewis acid ZnCl2 catalyzed [4+1] annulation of alkylthio-substituted enaminones is reported, that is, α-oxo ketene N,S-acetals with sulfur ylides to afford 2-acyl-3-aminofuran derivatives. In a similar fashion, [4+1] annulation of the corresponding enaminothiones, that is, α-thioxo ketene N,S-acetals, with sulfur ylides efficiently proceeded to give multisubstituted 3-aminothiophenes. This method features wide substrate scopes as well as broad functional group tolerance, offering a concise route to highly functionalized furans and thiophenes. 相似文献
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Virginie Blot Jean-François Brièr Marion Davoust Stéphanie Minière Vincent Reboul Patrick Metzner 《Phosphorus, sulfur, and silicon and the related elements》2013,188(5-6):1171-1182
Abstract Our work on the thio-Claisen rearrangement mediated by an adjacent sulfinyl group is reviewed. The substrates could easily be prepared on a large scale from diacetone-D-glucose. The rearrangement was effected with a diastereoselectivity of 95:5, in favor of the (S,S) or the (R,R) isomer. An approach to natural bis(lactones) was investigated, using a halolactonization reaction and a second [3,3] sigmatropic shift, again mediated by the sulfinyl group. The second part deals with the catalytic enantioselective benzylidenation of aldehydes, mediated by chiral sulfur ylides. We have introduced simple C 2 symmetric thiolanes for that purpose. The procedure is very practical and enantiomeric excesses up to 96% have been reported for the model of stilbene oxide. A series of ferrocenyl sulfides with planar chirality has also been investigated, leading to unexpected diastereoselectivities and enantiomeric excesses up to 94%. 相似文献
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QQ Yang C Xiao LQ Lu J An F Tan BJ Li WJ Xiao 《Angewandte Chemie (International ed. in English)》2012,51(36):9137-9140
Batting the ylides: A simple procedure carried out under mild conditions allows the direct and efficient synthesis of structurally diverse indoles. This approach involves a cascade reaction of sulfur ylides and N-(ortho-chloromethyl)aryl amides. 相似文献
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Prithwish Ghosh Na Yeon Kwon Saegun Kim Sangil Han Suk Hun Lee Won An Neeraj Kumar Mishra Soo Bong Han In Su Kim 《Angewandte Chemie (International ed. in English)》2021,60(1):191-196
The direct methylation of N‐heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp2)‐H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional‐group tolerance were attained. Moreover, this method can be readily applied to the site‐selective methylation of azauracil nucleosides. The feasibility of gram‐scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium‐labeling experiments aided the elucidation of a plausible reaction mechanism. 相似文献