A study of hydroboration of alkenes and alkynes with pinacolborane catalyzed by transition metals

被引：173

作者：

Pereira, S ^{[1
]}

Srebnik, M ^{[1
]}

机构：

[1] UNIV TOLEDO,DEPT CHEM,TOLEDO,OH 43606

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 19期

关键词：

D O I：

10.1016/0040-4039(96)00576-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pinacolborane (PBH) is an excellent stoichiometric hydroboration reagent for alkenes and alkynes in the presence of catalytic amounts of transition metals. While Wilkinson's catalyst causes isomerization of internal alkenes, Rh(CO)(PPh(3))(2)Cl gives the internal alkyl pinacolboronates in excellent regioselectivity. Rhodium and also nickel are extremely effective catalysts for the hydroboration of alkynes with PBH. (C) 1996 Elsevier Science Ltd.

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页码：3283 / 3286

页数：4

相关论文

共 22 条

[1] COINAGE METAL-CATALYZED HYDROBORATION OF IMINES [J].

BAKER, RT ;

CALABRESE, JC ;

WESTCOTT, SA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 498 (02) :109-117

[2] HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE [J].

BROWN, HC ;

GUPTA, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) :5249-5255

[3] HYDROBORATION .27. HYDROBORATION OF 1-BUTENYL AND RELATED VINYL DERIVATIVES CONTAINING REPRESENTATIVE SUBSTITUENTS . AN UNUSUALLY POWERFUL DIRECTIVE INFLUENCE OF ETHOXY SUBSTITUENT [J].

BROWN, HC ;

SHARP, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (11) :2915-+

[4] VINYLBORANE FORMATION IN RHODIUM-CATALYZED HYDROBORATION OF VINYLARENES - MECHANISM VERSUS BORANE STRUCTURE AND RELATIONSHIP TO SILATION [J].

BROWN, JM ;

LLOYDJONES, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :866-878

[5] TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].

BURGESS, K ;

OHLMEYER, MJ .

CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191

[6] REACTIONS OF CATECHOLBORANE WITH WILKINSON CATALYST - IMPLICATIONS FOR TRANSITION METAL-CATALYZED HYDROBORATIONS OF ALKENES [J].

BURGESS, K ;

VANDERDONK, WA ;

WESTCOTT, SA ;

MARDER, TB ;

BAKER, RT ;

CALABRESE, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9350-9359

[7] MECHANISTIC STUDY OF THE RHODIUM(I)-CATALYZED HYDROBORATION REACTION [J].

EVANS, DA ;

FU, GC ;

ANDERSON, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6679-6685

[8]

KOBAYASHI Y, 1995, SYNLETT, P571

[9] CATALYTIC HYDROBORATION WITH RHODIUM COMPLEXES [J].

MANNIG, D ;

NOTH, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (10) :878-879

[10] ALPHA-HALO BORONIC ESTERS - INTERMEDIATES FOR STEREODIRECTED SYNTHESIS [J].

MATTESON, DS .

CHEMICAL REVIEWS, 1989, 89 (07) :1535-1551