Synthesis of Functionalized 2-Arylthiophenes with Triarylbismuths as Atom-Efficient Multicoupling Organometallic Nucleophiles under Palladium Catalysis

被引:19
作者
Rao, Maddali L. N. [1 ]
Banerjee, Debasis [1 ]
Dhanorkar, Ritesh J. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
2-halothiophenes; cross-coupling; palladium catalysis; triarylbismuths; atom-efficient; multicoupling; CROSS-COUPLING REACTIONS; SUZUKI-MIYAURA REACTIONS; ARYL HALIDES; THIOPHENE; DERIVATIVES; CHLORIDES; REAGENTS; DESIGN; ACID; INHIBITORS;
D O I
10.1055/s-0030-1260554
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Atom-efficient cross-coupling reactions of functionalized 2-bromo- and 2-iodothiophenes have been demonstrated using triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium-catalyzed conditions. These couplings with various functionalized triarylbismuths proceeded smoothly to afford the corresponding functionalized 2-arylthiophenes in high yields.
引用
收藏
页码:1324 / 1330
页数:7
相关论文
共 68 条
[41]   Atom-efficient cross-coupling reactions of triarylbismuths with acyl chlorides under Pd(0) catalysis [J].
Rao, Maddah L. N. ;
Venkatesh, Varadhachari ;
Banerjee, Debasis .
TETRAHEDRON, 2007, 63 (52) :12917-12926
[42]   An atom-efficient palladium-catalyzed cross-coupling reaction of triarylbismuths with acid chlorides: synthesis of diaryl and alkyl aryl ketones [J].
Rao, Maddah L. N. ;
Venkatesh, Varadhachari ;
Jadhav, Deepak N. .
TETRAHEDRON LETTERS, 2006, 47 (39) :6975-6978
[43]   A palladium catalyzed atom-efficient cross-coupling reactivity of triarylbismuths with α,β-unsaturated acyl chlorides [J].
Rao, Maddali L. N. ;
Venkatesh, Varadhachari ;
Jadhav, Deepak N. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (15) :2494-2498
[44]   A new palladium catalyzed protocol for atom-efficient cross-coupling reactions of triarylbismuths with aryl halides and triflates [J].
Rao, Maddali L. N. ;
Jadhav, Deepak N. ;
Banerjee, Debasis .
TETRAHEDRON, 2008, 64 (24) :5762-5772
[45]   Palladium catalyzed atom-efficient cross-coupling reactions of triarylbismuths with aryl iodides and aryl triflates [J].
Rao, Maddali L. N. ;
Banerjee, Debasis ;
Jadhav, Deepak N. .
TETRAHEDRON LETTERS, 2007, 48 (38) :6644-6647
[46]   Palladium catalyzed atom-efficient cross-coupling reactions of triarylbismuths with aryl bromides [J].
Rao, Maddali L. N. ;
Banerjee, Debasis ;
Jadhav, Deepak N. .
TETRAHEDRON LETTERS, 2007, 48 (15) :2707-2711
[47]   Palladium-Catalyzed Synthesis of 4-Arylcoumarins Using Triarylbismuth Compounds as Atom-Efficient Multicoupling Organometallic Nucleophiles [J].
Rao, Maddali L. N. ;
Venkatesh, Varadhachari ;
Jadhav, Deepak N. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (20) :3945-3955
[48]   Pd(0)-catalyzed couplings using bromide and chloride derivatives of Baylis-Hillman adducts with triarylbismuths as atom-efficient multi-coupling nucleophiles [J].
Rao, Maddali L. N. ;
Banerjee, Debasis ;
Dhanorkar, Ritesh J. .
TETRAHEDRON, 2010, 66 (20) :3623-3632
[49]   Palladium-catalyzed cross-couplings of allylic carbonates with triarylbismuths as multi-coupling atom-efficient organometallic nucleophiles [J].
Rao, Maddali L. N. ;
Banerjee, Debasis ;
Giri, Somnath .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (10-11) :1518-1525
[50]   Pd-Catalyzed Domino Synthesis of Internal Alkynes Using Triarylbismuths as Multicoupling Organometallic Nucleophiles [J].
Rao, Maddali L. N. ;
Jadhav, Deepak N. ;
Dasgupta, Priyabrata .
ORGANIC LETTERS, 2010, 12 (09) :2048-2051