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Frontispiece: Rhodium Enalcarbenoids: Direct Synthesis of Indoles by Rhodium(II)‐Catalyzed [4+2] Benzannulation of Pyrroles 下载免费PDF全文
Sudam Ganpat Dawande Vinaykumar Kanchupalli Jagadeesh Kalepu Haribabu Chennamsetti Bapurao Sudam Lad Dr. Sreenivas Katukojvala 《Angewandte Chemie (International ed. in English)》2014,53(16)
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Direct Synthesis of 5‐Aryl Barbituric Acids by Rhodium(II)‐Catalyzed Reactions of Arenes with Diazo Compounds 下载免费PDF全文
Dr. Daniel Best Dr. David J. Burns Prof. Hon Wai Lam 《Angewandte Chemie (International ed. in English)》2015,54(25):7410-7413
A commercially available rhodium(II) complex catalyzes the direct arylation of 5‐diazobarbituric acids with arenes, allowing straightforward access to 5‐aryl barbituric acids. Free N? H groups are tolerated on the barbituric acid, with no complications arising from N? H insertion processes. This method was applied to the concise synthesis of a potent matrix metalloproteinase (MMP) inhibitor. 相似文献
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Dr. Xiaoxun Li Dr. Haibo Xie Xiaoning Fu Ji‐tian Liu Hao‐yuan Wang Prof. Dr. Bao‐min Xi Prof. Dr. Peng Liu Prof. Dr. Xiufang Xu Prof. Dr. Weiping Tang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(30):10410-10414
A de novo synthesis of a benzene ring allows for the preparation of a diverse range of heterocycles including indoles, benzofurans, benzothiophenes, carbazoles, and dibenzofurans from simple heteroaryl propargylic esters using a unified carbonylative benzannulation strategy. Multiple substituents can be easily introduced to the C4–C7 positions of indoles and related heterocycles. 相似文献
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Rhodium(II)‐Catalyzed Annulation of Azavinyl Carbenes Through Ring‐Expansion of 1,3,5‐Trioxane: Rapid Access to Nine‐Membered 1,3,5,7‐Trioxazonines 下载免费PDF全文
Dr. Jola Pospech Dr. Raffaella Ferraccioli Dr. Helfried Neumann Prof. Dr. Matthias Beller 《化学:亚洲杂志》2015,10(12):2624-2630
The rhodium(II)‐catalyzed denitrogenative coupling of N‐alkylsulfonyl 1,2,3‐triazoles with 1,3,5‐trioxane led to nine‐membered‐ringed trioxazonines in moderate‐to‐good yields. 1,3,5‐Trioxane, acting as an oxygen nucleophile, reacted with the α‐aza‐vinylcarbene intermediate, giving rise to ylide formation, which was probably the key step in the reaction. Triazoles that contained aryl substituents with various electronic and steric features on the C4 carbon atom were well‐tolerated. The synthesis of trioxazonine derivatives was achieved through a one‐pot, two‐step procedure from 1‐mesylazide and a terminal alkyne by combining CuI‐catalyzed 1,3‐dipolar cycloaddition and rhodium‐catalyzed transformations. 相似文献
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Rhodium(III)‐Catalyzed [3+2] Annulation of 5‐Aryl‐2,3‐dihydro‐1H‐pyrroles with Internal Alkynes through C(sp2)H/Alkene Functionalization 下载免费PDF全文
Ming‐Bo Zhou Rui Pi Ming Hu Yuan Yang Ren‐Jie Song Dr. Yuanzhi Xia Prof. Dr. Jin‐Heng Li 《Angewandte Chemie (International ed. in English)》2014,53(42):11338-11341
This study describes a new rhodium(III)‐catalyzed [3+2] annulation of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp2)? H bond and addition/protonolysis of an alkene C?C bond. This method is applicable to a wide range of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles and internal alkynes, and results in the assembly of the spiro[indene‐1,2′‐pyrrolidine] architectures in good yields with excellent regioselectivities. 相似文献
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A [4+1] Cyclative Capture Approach to 3H‐Indole‐N‐oxides at Room Temperature by Rhodium(III)‐Catalyzed CH Activation 下载免费PDF全文
Dr. Yaxi Yang Xuan Wang Dr. Yuanchao Li Dr. Bing Zhou 《Angewandte Chemie (International ed. in English)》2015,54(51):15400-15404
The rhodium(III)‐catalyzed [3+2] C? H cyclization of aniline derivatives and internal alkynes represents a useful contribution to straightforward synthesis of indoles. However, there is no report on the more challenging synthesis of pharmaceutically important N‐hydroxyindoles and 3H‐indole‐N‐oxides. Reported herein is the first rhodium(III)‐catalyzed [4+1] C? H oxidative cyclization of nitrones with diazo compounds to access 3H‐indole‐N‐oxides. More significantly, this reaction proceeds at room temperature and has been extended to the synthesis of N‐hydroxyindoles and N‐hydroxyindolines. 相似文献
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The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(II)‐Catalyzed Cycloadditions of 1‐Sulfonyl 1,2,3‐Triazoles with 1,3‐Dienes 下载免费PDF全文
Dr. Hai Shang Yuanhao Wang Dr. Yu Tian Juan Feng Prof. Dr. Yefeng Tang 《Angewandte Chemie (International ed. in English)》2014,53(22):5662-5666
The first rhodium(II)‐catalyzed aza‐[4+3] cycloadditions of 1‐sulfonyl 1,2,3‐triazoles with 1,3‐dienes have been developed, and enable the efficient synthesis of highly functionalized 2,5‐dihydroazepines from readily available precursors. In some cases, the reaction pathway could divert to formal aza‐[3+2] cycloadditions, thus leading to 2,3‐dihydropyrroles. In this context, the titled reaction represents a capable tool for the divergent synthesis of two types of synthetically valuable aza‐heterocycles from common rhodium(II) iminocarbene intermediates. 相似文献
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Dirhodium(II)‐Catalyzed Annulation of Enoldiazoacetamides with α‐Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring Systems 下载免费PDF全文
Dr. Qing‐Qing Cheng Julietta Yedoyan Dr. Hadi Arman Prof. Dr. Michael P. Doyle 《Angewandte Chemie (International ed. in English)》2016,55(18):5573-5576
A dirhodium(II)‐catalyzed annulation reaction between two structurally different diazocarbonyl compounds furnishes the donor–acceptor cyclopropane‐fused benzoxa[3.2.1]octane scaffold with excellent chemo‐, regio‐, and diastereoselectivity under exceptionally mild conditions. The composite transformation occurs by [3+2]‐cycloaddition between donor–acceptor cyclopropenes generated from enoldiazoacetamides and carbonyl ylides formed from intramolecular carbene–carbonyl cyclization in one pot with one catalyst. The annulation products can be readily transformed into benzoxa[3.3.1]nonane and hexahydronaphthofuran derivatives with exact stereocontrol. This method allows the efficient construction of three fused and bridged ring systems, all of which are important skeletons of numerous biologically active natural products. 相似文献
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Rhodium(II)‐Catalyzed Intramolecular Cycloisomerizations of Methylenecyclopropanes with N‐Sulfonyl 1,2,3‐Triazoles 下载免费PDF全文
Kai Chen Zi‐Zhong Zhu Yong‐Sheng Zhang Dr. Xiang‐Ying Tang Prof. Min Shi 《Angewandte Chemie (International ed. in English)》2014,53(26):6645-6649
A novel rhodium(II)‐catalyzed tandem cycloisomerization of methylenecyclopropanes (MCPs) with N‐sulfonyl 1,2,3‐triazoles is disclosed. The reaction produces a series of highly functionalized polycyclic N heterocycles via a rhodium imino carbene intermediate. A distinct feature of this divergent synthesis is that different types of substrates control the reaction pathways. Moreover, several interesting transformations of these products to construct diazabicyclo[3.2.1]octane derivatives are also reported. 相似文献
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Rhodium(II)‐Catalyzed Intramolecular Annulation of 1‐Sulfonyl‐1,2,3‐Triazoles with Pyrrole and Indole Rings: Facile Synthesis of N‐Bridgehead Azepine Skeletons 下载免费PDF全文
Jin‐Ming Yang Cheng‐Zhi Zhu Dr. Xiang‐Ying Tang Prof. Dr. Min Shi 《Angewandte Chemie (International ed. in English)》2014,53(20):5142-5146
A convenient and efficient synthetic method has been developed to construct highly functionalized N‐bridgehead azepine skeletons, which are of great importance in biological and pharmaceutical industry. The reaction proceeds through a rhodium(II) azavinyl carbene intermediate, which initiated the intramolecular C? H functionalization with pyrrolyl and indolyl rings. A variety of azepine derivatives were obtained in moderate to good yields under mild reaction conditions with high chemoselectivity. Several interesting derivatizations of the resulting products demonstrate that this method is synthetically valuable and useful. 相似文献
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Sheng Feng Prof. Fanyang Mo Dr. Ying Xia Zhenxing Liu Zhen Liu Prof. Yan Zhang Prof. Jianbo Wang 《Angewandte Chemie (International ed. in English)》2016,55(49):15401-15405
The rhodium(I)‐catalyzed C?C bond activation reaction of siloxyvinylcyclopropanes with diazoesters demonstrates a novel mode of C?C bond cleavage of siloxyvinvylcyclopanes. The alkene products were obtained as single E‐configured isomers in good yields. A σ,η3‐allyl rhodium complex, which has been previously proposed as the key intermediate in rhodium(I)‐catalyzed cycloaddition of vinylcyclopropanes, has been isolated and characterized by X‐ray crystallography. 相似文献
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Thermally Induced Denitrogenative Annulation for the Synthesis of Dihydroquinolinimines and Chroman‐4‐imines 下载免费PDF全文
Chih‐Hung Chou Ying‐Yu Chen Basker Rajagopal Hsiu‐Chung Tu Kuan‐Lin Chen Sheng‐Fu Wang Chien‐Fu Liang Prof. Yu‐Chang Tyan Prof. Po‐Chiao Lin 《化学:亚洲杂志》2016,11(5):757-765
A rapid growth in synthetic methods for the preparation of diverse organic molecules using N‐sulfonyl‐1,2,3‐triazoles is of great interest in organic synthesis. Transition metals are generally used to activate the α‐imino diazo intermediates. Metal‐free methods have not been studied in detail, but can be a good complement to transition metal catalysis in the mild reaction conditions. We herein report a novel method for the preparation of 2,3‐dihydroquinolin‐4‐imine and chroman‐4‐imine analogs from their corresponding N‐sulfonyl‐1,2,3‐triazoles in the absence of metal catalysts. To achieve intramolecular annulation, the introduction of an electron‐donating group is required at the meta position of N‐sulfonyl‐1,2,3‐triazole methyl anilines. The inclusion of tailored substituents on the aniline moieties and nitrogen atoms enhances the nucleophilicity of the phenyl π‐electrons, thus allowing them to undergo a Friedel–Crafts‐type reaction with the highly electrophilic ketenimines. This metal‐free method was carefully optimized to generate a variety of dihydroquinolin‐4‐imines and chroman‐4‐imines in moderate‐to‐good yields. 相似文献
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《化学:亚洲杂志》2017,12(18):2383-2387
Efficient [Cu(NHC)]‐catalyzed syntheses of pyrroles via two and three‐component coupling methods are described. Various 1,2‐, 1,2,3‐, 1,2,3,5‐ and fully substituted pyrroles were readily accessible through a suitable choice of ketone, primary amine and diol in a three‐component reaction. The N‐unsubstituted pyrrole formation is also feasible through a two‐component reaction involving a β‐amino alcohol and a ketone. 相似文献
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Copper‐Catalyzed (2+1) Annulation of Acetophenones with Maleimides: Direct Synthesis of Cyclopropanes 下载免费PDF全文
Srimanta Manna Dr. Andrey P. Antonchick 《Angewandte Chemie (International ed. in English)》2015,54(49):14845-14848
A practical copper‐catalyzed direct oxidative cyclopropanation of electron‐deficient alkenes with acetophenone derivatives is reported. The dehydrogenative annulation involves a double C? H bond functionalization at the α‐position of the ketone using di‐tert‐butyl peroxide as oxidant. The broad scope of the reaction and excellent functional‐group tolerance is demonstrated for the stereoselective synthesis of fused cyclopropanes. The developed transformation revealed an unprecedented reactivity for copper‐catalyzed processes. 相似文献