Direct synthesis of highly substituted thiophenes through copper(i)-catalyzed tandem reactions of alkylidenethiiranes with terminal alkynes.

A novel copper(i)-catalyzed tandem addition/cycloisomerization reaction of 1-phenylsulfonylalkylidenethiiranes with terminal alkynes for the convergent assembly of 2-(alpha-phenylsulfonylalkyl)-thiophenes is reported, which could directly assemble various functional groups incorporated into the thiophene ring.

[1]  M. Xian,et al.  Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes. , 2009, Organic letters.

[2]  Chang-Qi Ma,et al.  Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. , 2009, Chemical reviews.

[3]  P. Knochel,et al.  Regio- and chemoselective synthesis of fully substituted thiophenes. , 2009, Organic letters.

[4]  Duanjun Xu,et al.  Thiazepine moiety-controlled regioselective rearrangements of 7-oxanorbornadiene derivatives. , 2008, Chemical communications.

[5]  M. Kaneko,et al.  Indium-catalyzed annulation of 2-aryl- and 2-heteroarylindoles with propargyl ethers: concise synthesis and photophysical properties of diverse aryl- and heteroaryl-annulated[a]carbazoles. , 2008, Journal of the American Chemical Society.

[6]  Itaru Osaka,et al.  Advances in molecular design and synthesis of regioregular polythiophenes. , 2008, Accounts of chemical research.

[7]  G. Evano,et al.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. , 2008, Chemical reviews.

[8]  Yoshinori Yamamoto,et al.  Coinage metal-assisted synthesis of heterocycles. , 2008, Chemical reviews.

[9]  I. Yavari,et al.  Efficient synthesis of tetrasubstituted thiophenes by reaction of benzoyl isothiocyanates, ethyl bromopyruvate and enaminones , 2008 .

[10]  W. Yao,et al.  Concise assembly of highly substituted furan-fused 1,4-thiazepines and their Diels-Alder reactions with benzynes. , 2008, The Journal of organic chemistry.

[11]  Tao Cai,et al.  Addition of amines to nitriles catalyzed by ytterbium amides: an efficient one-step synthesis of monosubstituted N-arylamidines. , 2008, Organic letters.

[12]  F. Liang,et al.  Efficient one-pot synthesis of polyfunctionalized thiophenes via an amine-mediated ring opening of EWG-activated 2-methylene-1,3-dithioles. , 2007, Organic letters.

[13]  M. Xian,et al.  Solvent-controlled Csp2-->O silyl migration: the "one-pot" synthesis of 2,3-disubsituted thiophenes. , 2007, Organic letters.

[14]  C. Fu,et al.  Highly selective thiiranation of 1,2-allenyl sulfones with Br2 and Na2S2O3: mechanism and asymmetric synthesis of alkylidenethiiranes. , 2007, Angewandte Chemie.

[15]  D. Bouchu,et al.  Novel method of aromatic coupling between N-aryl methanesulfonamide and thiophene derivatives. , 2007, Organic letters.

[16]  S. Sasaki,et al.  Synthesis of dihydrothiophene, thiophene, and their selenium analogues carrying four phosphoryl groups. , 2007, Organic letters.

[17]  N. Fujii,et al.  Direct synthesis of 2-(aminomethyl)indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions. , 2007, Angewandte Chemie.

[18]  Yiping Zhang,et al.  A ring-expansion methodology involving multicomponent reactions: highly efficient access to polysubstituted furan-fused 1,4-thiazepine derivatives. , 2006, Angewandte Chemie.

[19]  I. Nakamura,et al.  Gold-catalyzed intramolecular carbothiolation of alkynes: synthesis of 2,3-disubstituted benzothiophenes from (alpha-alkoxy alkyl) (ortho-alkynyl phenyl) sulfides. , 2006, Angewandte Chemie.

[20]  Cheng Ma,et al.  Thiazolium-mediated multicomponent reactions: a facile synthesis of 3-aminofuran derivatives. , 2005, Organic letters.

[21]  S. Obrey,et al.  Concurrent tandem catalysis. , 2005, Chemical reviews.

[22]  E. N. Santos,et al.  Tandem catalysis: a taxonomy and illustrative review , 2004 .

[23]  Hoon Han,et al.  Cooperative multi-catalyst systems for one-pot organic transformations. , 2004, Chemical Society reviews.

[24]  I. Nakamura,et al.  Transition-metal-catalyzed reactions in heterocyclic synthesis. , 2004, Chemical reviews.

[25]  R. Larock,et al.  Synthesis of Heterocycles via Palladium π-Olefin and π-Alkyne Chemistry , 2004 .

[26]  P. R. Blakemore,et al.  The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds , 2002 .

[27]  E. N. Prilezhaeva Sulfones and sulfoxides in the total synthesis of biologically active natural compounds , 2000 .

[28]  Gabriele,et al.  Novel synthesis of substituted thiophenes by palladium-catalyzed cycloisomerization of (Z)-2-en-4-yne-1-thiols , 2000, Organic letters.

[29]  S. A. Burova,et al.  Sulfur-Alkyne Cyclizations for Formation of Dihydrothiophenes and Annulated Thiophenes , 2000 .

[30]  M. Yus,et al.  Desulfonylation reactions: Recent developments , 1999 .

[31]  S. Destri,et al.  Synthesis of 3,4-bis[(methoxycarbonyl)methyl]thiophene and bis-, ter- and pentathiophenes with alternating 3,4-bis[(methoxycarbonyl)methyl]-substituted rings , 1999 .

[32]  O. Tarasova,et al.  One‐Pot Syntheses of 2‐N‐Alkylamino‐, 2‐N‐Phenylamino‐, 2‐N, N‐Dialkylamino‐, and 2‐N‐Alkyl‐N‐phenylaminothiophenes , 1998 .

[33]  W. Dubay,et al.  A new synthesis of thiophenes through base-promoted cyclization of β- and γ-alkynyl thiols , 1993 .

[34]  J. Roncali Conjugated poly(thiophenes): synthesis, functionalization, and applications , 1992 .

[35]  Y. Kabe,et al.  Palladium(0)-catalyzed intra- and intermolecular cyclization reactions of allene episulfides , 1991 .