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.

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收藏

页码：1388 / 1390

页数：3

相关论文

共 20 条

[1] Synthesis of functionalised diarylmethanes via a cobalt-catalysed cross-coupling of arylzinc species with benzyl chlorides [J].

Amatore, Muriel ;

Gosmini, Corinne .

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 [J].

Burns, Michael J. ;

Fairlamb, Ian J. S. ;

Kapdi, Anant R. ;

Sehnal, Petr ;

Taylor, Richard J. K. .

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 [J].

Choudhury, J ;

Podder, S ;

Roy, S .

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 [J].

Kobayashi, T ;

Rahman, SM .

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 [J].

Kuwano, R ;

Kondo, Y ;

Shirahama, T .

ORGANIC LETTERS, 2005, 7 (14) :2973-2975

[9] Selective double Suzuki cross-coupling reactions.: Synthesis of unsymmetrical diaryl (or heteroaryl) methanes [J].

Langle, S ;

Abarbri, M ;

Duchêne, A .

TETRAHEDRON LETTERS, 2003, 44 (52) :9255-9258

[10] Tetraorganoindates as nucleophilic coupling partners in Pd-catalyzed cross-coupling reactions [J].

Lee, PH ;

Lee, SW ;

Seomoon, D .

ORGANIC LETTERS, 2003, 5 (26) :4963-4966