Evidence for the formation and structure of palladacycles during Pd-catalyzed C-N bond formation with catalysts derived from bulky monophosphinobiaryl ligands

被引：71

作者：

Strieter, ER ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 06期

关键词：

aminations; cross-coupling; palladium; phosphanes;

D O I：

10.1002/anie.200502927

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The structural origins of the differences in catalytic activity observed between catalysts containing 2′-substituted and 2′,6′-disubstituted biaryl monophosphane ligands for a Pd-catalyzed C-N bond-forming reaction are discussed. It is shown that palladacycle formation is avoided and optimal catalyst activity is achieved through the use of the 2′,6′-disubstituted ligands. (tAm = tert-amyl, dppe = 1,2-bis(diphenylphosphanyl)-ethane). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：925 / 928

页数：4

相关论文

共 49 条

[31]

2-U

[32] A route to Pd-0 from Pd-II metallacycles in amination and cross-coupling chemistry [J].

Louie, J ;

Hartwig, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (20) :2359-2361

[33] Practical palladium catalysts for C-N and C-O bond formation [J].

Muci, AR ;

Buchwald, SL .

CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 :131-209

[34] The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates [J].

Nguyen, HN ;

Huang, XH ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11818-11819

[35] Cyclopalladated imine catalysts in Heck arylation: search for the catalytic species [J].

Nowotny, M ;

Hanefeld, U ;

van Koningsveld, H ;

Maschmeyer, T .

CHEMICAL COMMUNICATIONS, 2000, (19) :1877-1878

[36] A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides [J].

Old, DW ;

Wolfe, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) :9722-9723

[37] Kinetic studies of Heck coupling reactions using palladacycle catalysts: Experimental and kinetic modeling of the role of dimer species [J].

Rosner, T ;

Le Bars, J ;

Pfaltz, A ;

Blackmond, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :1848-1855

[38] Observation of unusual kinetics in Heck reactions of aryl halides: The role of non-steady-state catalyst concentration [J].

Rosner, T ;

Pfaltz, A ;

Blackmond, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4621-4622

[39] Palladium-catalyzed C-N and C-O coupling - A practical guide from an industrial vantage point [J].

Schlummer, B ;

Scholz, U .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1599-1626

[40]

Shilov A. E., 2000, ACTIVATION CATALYTIC

← 1 2 3 4 5 →