Microwave-promoted rhodium-catalyzed arylation of heterocycles through C-H bond activation

被引：126

作者：

Lewis, JC

Wu, JY

Bergman, RG ^{[1
]}

Ellman, JA

机构：

[1] Univ Calif Berkeley, Lawrence Berkeley Lab, Div Chem Sci, Dept Chem, Berkeley, CA 94720 USA

[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 10期

关键词：

arylation; C-H activation; heterocycles; phosphane ligands; rhodium;

D O I：

10.1002/anie.200504289

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Performance-enhancing ligands: Two new bridged bicyclic phosphines 1a,b based on the "phoban" skeleton (see structures of their naphth-2-ylmethyl bromide salts; P yellow, Br brown, C white) are central to a practical catalytic method for the direct arylation of a variety of nitrogen heterocycles using aryl bromides. Broad functional-group tolerance was observed, and the use of microwave radiation allowed for short reaction times. (Chemical Equation Presented) © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：1589 / 1591

页数：3

相关论文

共 33 条

[1] SUCCESSFUL APPLICATION OF A FORGOTTEN PHOSPHINE IN ASYMMETRIC CATALYSIS - A 9-PHOSPHABICYCLO[3.3.1]NON-9-YL FERROCENE DERIVATIVE AS CHIRAL LIGAND [J].

ABBENHUIS, HCL ;

BURCKHARDT, U ;

GRAMLICH, V ;

KOLLNER, C ;

PREGOSIN, PS ;

SALZMANN, R ;

TOGNI, A .

ORGANOMETALLICS, 1995, 14 (02) :759-766

[2] One-step synthesis of 2-arylbenzothiazole ('BTA') and -benzoxazole precursors for in vivo imaging of β-amyloid plaques [J].

Alagille, D ;

Baldwin, RM ;

Tamagnan, GD .

TETRAHEDRON LETTERS, 2005, 46 (08) :1349-1351

[3] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201

[4] SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].

ARNDTSEN, BA ;

BERGMAN, RG ;

MOBLEY, TA ;

PETERSON, TH .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162

[5] Syntheses of novel chiral monophosphines, 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes, and their application in highly enantioselective Pd-catalyzed allylic alkylations [J].

Chen, ZG ;

Jiang, QZ ;

Zhu, GX ;

Xiao, DM ;

Cao, P ;

Guo, C ;

Zhang, XM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4521-4523

[6] Palladium complexes of bridgehead phosphines [J].

Coles, SJ ;

Edwards, PG ;

Hursthouse, MB ;

Malik, KMA ;

Thick, JL ;

Tooze, RP .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (11) :1821-1830

[7] Alkane C-H activation and functionalization with homogeneous transition metal catalysts: a century of progress-a new millennium in prospect [J].

Crabtree, RH .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (17) :2437-2450

[8] A simple procedure for the separation of the catalytically important phosphabicyclononane isomers [J].

Downing, JH ;

Gee, V ;

Pringle, PG .

CHEMICAL COMMUNICATIONS, 1997, (16) :1527-1528

[9]

Dwyer C., UNPUB

[10]

Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO

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