Organoborane coupling reactions (Suzuki coupling)

被引：131

作者：

Suzuki, A ^{[1
]}

机构：

[1] Hokkaido Univ, Sapporo, Hokkaido 060, Japan

来源：

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES | 2004年 / 80卷 / 08期

关键词：

Pd-catalyst; cross-coupling reaction; organoboron compounds; synthesis of conjugated alkadienes and alkenynes; biaryl synthesis;

D O I：

10.2183/pjab.80.359

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

The palladium-catalyzed cross-coupling reaction between different types of organoboron 3 compounds with sp(2)-, sp(3)-, and sp-hybridized carbon-boron compounds and various organic electrophiles in the presence of base provides a powerful and useful synthetic methodology for the formation of carbon-carbon bonds. The coupling reaction offers several advantages: (1) Availability of reactants (2) Mild reaction conditions (3) Water stability (4) Easy use of the reaction both in aqueous and heterogeneous conditions (5) Tolerance of a broad range of functional groups (6) High regio- and stereoselectivity (7) Insignificant effect toward steric hindrance (8) Use of very small amounts of catalysts (9) Utilization as one-pot synthesis (10) Non-toxic reaction.

引用

页码：359 / 371

页数：13

共 43 条

[1]

ABRAHAM MH, 1985, CHEM METAL CARBON BO, P115

[2] TOTAL SYNTHESIS OF A FULLY PROTECTED PALYTOXIN CARBOXYLIC-ACID [J].

ARMSTRONG, RW ;

BEAU, JM ;

CHEON, SH ;

CHRIST, WJ ;

FUJIOKA, H ;

HAM, WH ;

HAWKINS, LD ;

JIN, H ;

KANG, SH ;

KISHI, Y ;

MARTINELLI, MJ ;

MCWHORTER, WW ;

MIZUNO, M ;

NAKATA, M ;

STUTZ, AE ;

TALAMAS, FX ;

TANIGUCHI, M ;

TINO, JA ;

UEDA, K ;

UENISHI, J ;

WHITE, JB ;

YONAGA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7525-7530

[3] Total synthesis of (-)-epothilone A [J].

Balog, A ;

Meng, DF ;

Kamenecka, T ;

Bertinato, P ;

Su, DS ;

Sorensen, EJ ;

Danishefsky, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2801-2803

[4] A convergent total synthesis of the michellamines [J].

Bringmann, G ;

Götz, R ;

Keller, PA ;

Walter, R ;

Boyd, MR ;

Lang, FR ;

Garcia, A ;

Walsh, JJ ;

Tellitu, I ;

Bhaskar, KV ;

Kelly, TR .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1090-1097

[5] Boronic ester as a linker system for solid phase synthesis [J].

Carboni, B ;

Pourbaix, C ;

Carreaux, F ;

Deleuze, H ;

Maillard, B .

TETRAHEDRON LETTERS, 1999, 40 (45) :7979-7983

[6]

Corriu R. J. P., 1972, J CHEM SOC CHEM COMM, V144

[7]

Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222

[8] PALLADIUM-CATALYZED ARYLATION OF POLAR ORGANOMETALLICS MEDIATED BY 9-METHOXY-9-BORABICYCLO[3.3.1]NONANE - SUZUKI REACTIONS OF EXTENDED SCOPE [J].

FURSTNER, A ;

SEIDEL, G .

TETRAHEDRON, 1995, 51 (41) :11165-11176

[9] APPROXIMATE SELF-CONSISTENT FIELD MOLECULAR-ORBITAL CALCULATIONS ON COMPLEXES OF TRIMETHYLBORON, BORON TRICHLORIDE, TRIMETHYLALUMINUM, ALANE AND ALUMINUM TRICHLORIDE WITH TRIMETHYLAMINE [J].

GROPEN, O ;

HAALAND, A .

ACTA CHEMICA SCANDINAVICA, 1973, 27 (02) :521-527

[10] Syntheses of phenothiazinylboronic acid derivatives -: Suitable starting points for the construction of redox active materials [J].

Krämer, CS ;

Zimmermann, TJ ;

Sailer, M ;

Müller, TJJ .

SYNTHESIS-STUTTGART, 2002, (09) :1163-1170

← 1 2 3 4 5 →