The palladium-catalyzed addition of organoboronic acids to alkynes

被引：160

作者：

Oh, CH ^{[1
]}

Jung, HH ^{[1
]}

Kim, KS ^{[1
]}

Kim, N ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Seoul 131791, South Korea

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 07期

关键词：

addition; alkynes; homogeneous catalysis; organoboronic acids; palladium;

D O I：

10.1002/anie.200390214

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

No base is necessary: Excellent yields are produced on addition of organoboronic acids to alkynes under mild reaction conditions when palladium compounds are used as catalysts (see scheme). Unlike the Suzuki-type cross-coupling reaction, the current reaction occurs in an acidic medium.

引用

收藏

页码：805 / 808

页数：4

相关论文

共 28 条

[1] Highly regio- and enantioselective catalytic hydrogenation of enamides in conjugated diene systems:: Synthesis and application of γ,δ-unsaturated amino acids [J].

Burk, MJ ;

Allen, JG ;

Kiesman, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :657-663

[2] PALLADIUM-CATALYZED CONJUGATED DIENE SYNTHESIS FROM VINYLIC HALIDES AND OLEFINIC COMPOUNDS [J].

DIECK, HA ;

HECK, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08) :1083-1090

[3] Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].

Hayashi, T ;

Inoue, K ;

Taniguchi, N ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919

[4] Rhodium-catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates [J].

Hayashi, T ;

Senda, T ;

Takaya, Y ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11591-11592

[5] CATALYTIC ASYMMETRIC-SYNTHESIS OF AXIALLY CHIRAL BIARYLS BY PALLADIUM-CATALYZED ENANTIOPOSITION-SELECTIVE CROSS-COUPLING [J].

HAYASHI, T ;

NIIZUMA, S ;

KAMIKAWA, T ;

SUZUKI, N ;

UOZUMI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9101-9102

[6] Stereoselective formation of 1,2-diiodoalkenes and their application in the stereoselective synthesis of highly functionalised alkenes via Suzuki and Stille coupling reactions [J].

Hénaff, N ;

Whiting, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :395-400

[7] Nickel catalyzed reactions of nucleophiles with unactivated and partially activated olefins and acetylenes [J].

Houpis, IN ;

Lee, J .

TETRAHEDRON, 2000, 56 (06) :817-846

[8] Enantioposition-selective arylation of biaryl ditriflates by palladium-catalyzed asymmetric Grignard cross-coupling [J].

Kamikawa, T ;

Hayashi, T .

TETRAHEDRON, 1999, 55 (11) :3455-3466

[9] Organozinc mediated reactions [J].

Knochel, P ;

Perea, JJA ;

Jones, P .

TETRAHEDRON, 1998, 54 (29) :8275-8319

[10] Regioselective rhodium-catalyzed addition of arylboronic acids to alkynes with a pyridine-substituted water-soluble ligand [J].

Lautens, M ;

Yoshida, M .

ORGANIC LETTERS, 2002, 4 (01) :123-125