Csp3-Csp2 Palladium-Catalyzed Cross-Coupling Reaction of Trialkylbismuth Reagents with Aryl, Heteroaryl, and Vinyl Halides and Triflates

被引：18

作者：

Gagnon, Alexandre ^{[1
]}

Albert, Vincent ^{[1
]}

Duplessis, Martin ^{[1
]}

机构：

[1] Boehringer Ingelheim Canada Ltd, Res & Dev, Laval, PQ H7S 2G5, Canada

来源：

SYNLETT | 2010年 / 19期

关键词：

cross-coupling; organometallic reagents; palladium; halides; catalysis; DEFICIENT OLEFIN LIGAND; ORGANOBISMUTH REAGENTS; ALKYLZINC REAGENTS; ROOM-TEMPERATURE; BROMIDES; IODIDES; TRIARYLBISMUTHS; DIALKOXIDES; CHEMISTRY; CHLORIDES;

D O I：

10.1055/s-0030-1259023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed cross-coupling reaction of trialkylbismuth reagents with aryl and heteroaryl halides and triflates is reported. Moderate to good yields were obtained for the transfer of primary alkyl groups. The reaction tolerates numerous functional groups on the electrophilic and nucleophilic partners. The cross-coupling of alpha-bromostyrene with tris(1,3-dioxan-2-ylethyl) bismuth is also reported.

引用

页码：2936 / 2940

页数：5

共 50 条

[21] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
Schmink, Jason R.
Krska, Shane W.
Tudge, Matthew T.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[22] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
ALHASSAN, MI
SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420
[23] Organophotocatalyzed E and Z stereoselective Csp3-Csp2 bond forming cross coupling reactions of carboxylic acids with β -aryl-vinyl halides
Huang, He
Zhang, Yueteng
Ji, Peng
Mariano, Patrick S.
Wang, Wei
GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (01): : 27 - 31
[24] UNSYMMETRICAL HETEROBIARYL SYNTHESIS - A HIGHLY EFFICIENT PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF HETEROARYL TRIALKYLSTANNANES WITH ARYL HALIDES
BAILEY, TR
TETRAHEDRON LETTERS, 1986, 27 (37) : 4407 - 4410
[25] Palladium-catalyzed cross-coupling reactions of in situ generated allylindium reagents with aryl halides
Lee, PH
Sung, SY
Lee, K
ORGANIC LETTERS, 2001, 3 (20) : 3201 - 3204
[26] Palladium-Catalyzed Cross-Coupling of Unsaturated Phenols with Vinylic Halides and Triflates
Larock, R. C.
Yang, H.
Pace, P.
Cacchi, S.
Tetrahedron Letters, 39 (3-4):
[27] Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides.
Minehan, TG
Lehmann, U
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U397 - U397
[28] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES
ALAMI, M
FERRI, F
LINSTRUMELLE, G
TETRAHEDRON LETTERS, 1993, 34 (40) : 6403 - 6406
[29] D-Glucosamine as a Green Ligand for Palladium-Catalyzed Cross-Coupling of Aryl and Heteroaryl Halides
Jha, Abadh Kishor
Shahni, Rahul Kumar
Jain, Nidhi
SYNLETT, 2015, 26 (02) : 259 - 264
[30] Palladium-catalyzed cross-coupling of unsaturated phenols with vinylic halides and triflates
Larock, RC
Yang, H
Pace, P
Cacchi, S
Fabrizi, G
TETRAHEDRON LETTERS, 1998, 39 (3-4) : 237 - 240

← 1 2 3 4 5 →