Atom-Efficient Vinylic Arylations with Triarylbismuths as Substoichiometric Multicoupling Reagents under Palladium Catalysis

被引:35
作者
Rao, Maddali L. N. [1 ]
Jadhav, Deepak N. [1 ]
Venkatesh, Varadhachari [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
Arylation; Bismuth; Palladium; Atom efficiency; Cross-coupling; CROSS-COUPLING REACTIONS; GRIGNARD-REAGENTS; ORGANOBISMUTH DIALKOXIDES; ARYLBORONIC ACIDS; ORGANIC-SYNTHESIS; FACILE SYNTHESIS; ACYL CHLORIDES; ARYL BROMIDES; TIN REAGENTS; HALIDES;
D O I
10.1002/ejoc.200900487
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first atom-efficient arylation of vinylic iodides was achieved by using triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis. Vinylic iodides were efficiently coupled with electronically divergent triarylbismuths to furnish the corresponding arylated products in short reaction times. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:4300 / 4306
页数:7
相关论文
共 54 条
[11]   Ring selectivity in the Na/EtOH reduction of 1-aryl-7-methoxynaphthalenes [J].
Carreño, MC ;
González-López, M ;
Latorre, A ;
Urbano, A .
SYNLETT, 2005, (10) :1601-1605
[12]   Selected patented cross-coupling reaction technologies [J].
Corbet, Jean-Pierre ;
Mignani, Gerard .
CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710
[13]   Potassium organotrifluoroborates: New perspectives in organic synthesis [J].
Darses, Sylvain ;
Genet, Jean-Pierre .
CHEMICAL REVIEWS, 2008, 108 (01) :288-325
[14]   Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods [J].
Denmark, Scott E. ;
Regen, Christopher S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1486-1499
[15]  
Dohle W, 2001, SYNLETT, P1901
[16]   Palladium-catalyzed stille cross-couplings of sulfonyl chlorides and organostannanes [J].
Dubbaka, SR ;
Vogel, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) :15292-15293
[17]   Synthesis of novel retinoid X receptor-selective retinoids [J].
Faul, MM ;
Ratz, AM ;
Sullivan, KA ;
Trankle, WG ;
Winneroski, LL .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5772-5782
[18]   Nonlinear solvent water effects in the excited-state (formal) intramolecular proton transfer (ESIPT) in m-hydroxy-1,1-diaryl alkenes:: Efficient formation of m-quinone methides [J].
Fischer, M ;
Wan, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (19) :4555-4562
[19]   Direct synthesis of 1,1-diarylalkenes from alkenyl phosphates via nickel(0)-catalysed Suzuki-Miyaura coupling [J].
Hansen, Anders L. ;
Ebran, Jean-Philippe ;
Gogsig, Thomas M. ;
Skrydstrup, Troels .
CHEMICAL COMMUNICATIONS, 2006, (39) :4137-4139
[20]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469