Palladium-Catalyzed Cross-Coupling Reactions of Benzyl Indium Reagents with Aryl Iodides

被引：43

作者：

Chupak, Louis S. ^{[1
]}

Wolkowski, Joanna P. ^{[1
]}

Chantigny, Yves A. ^{[1
]}

机构：

[1] Pfizer Inc, Groton Labs, Groton, CT 06340 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期

关键词：

ARYLBORONIC ACIDS; HALIDES; DIARYLMETHANES; ORGANOMETALLICS; ALKYLATION; HETEROARYL; CHLORIDES; PARTNERS; METAL;

D O I：

10.1021/jo802280m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein described is an operationally simple procedure for generating benzyl indium species from readily available benzyl bromides and indium metal followed by in situ palladium-catalyzed coupling with aryl halides. The procedure provides diarylmethanes in modest to excellent yield and tolerates a variety of functional groups in both coupling partners.

引用

页码：1388 / 1390

页数：3

共 20 条

[1] Synthesis of functionalised diarylmethanes via a cobalt-catalysed cross-coupling of arylzinc species with benzyl chlorides
Amatore, Muriel
Gosmini, Corinne
[J]. CHEMICAL COMMUNICATIONS, 2008, (40) : 5019 - 5021
[2] Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners
Burns, Michael J.
Fairlamb, Ian J. S.
Kapdi, Anant R.
Sehnal, Petr
Taylor, Richard J. K.
[J]. ORGANIC LETTERS, 2007, 9 (26) : 5397 - 5400
[3] Chahen L, 2003, SYNLETT, P1668
[4] Cooperative Friedel-Crafts catalysis in heterobimetallic regime:: Alkylation of aromatics by π-activated alcohols
Choudhury, J
Podder, S
Roy, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) : 6162 - 6163
[5] Hermite N. L., 2006, TETRAHEDRON, V62, P11994
[6] A simple preparation of diarylmethanes by oxidative friedel-crafts reaction of methyl-substituted benzenes with o-chloranil
Kobayashi, T
Rahman, SM
[J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (22) : 3997 - 4003
[7] Ku YY, 1996, TETRAHEDRON LETT, V37, P1949
[8] Transformation of carbonates into sulfones at the benzylic position via palladium-catalyzed benzylic substitution
Kuwano, R
Kondo, Y
Shirahama, T
[J]. ORGANIC LETTERS, 2005, 7 (14) : 2973 - 2975
[9] Selective double Suzuki cross-coupling reactions.: Synthesis of unsymmetrical diaryl (or heteroaryl) methanes
Langle, S
Abarbri, M
Duchêne, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (52) : 9255 - 9258
[10] Tetraorganoindates as nucleophilic coupling partners in Pd-catalyzed cross-coupling reactions
Lee, PH
Lee, SW
Seomoon, D
[J]. ORGANIC LETTERS, 2003, 5 (26) : 4963 - 4966

← 1 2 →