Highly Efficient Synthesis of Alkylboronate Esters via Cu(II)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides in Air

被引：116

作者：

Bose, Shubhankar Kumar ^{[1
,2
]}

Brand, Simon ^{[1
,2
]}

Omoregie, Helen Oluwatola ^{[4
]}

Haehnel, Martin ^{[1
,2
]}

Maier, Jonathan ^{[3
]}

Bringmann, Gerhard ^{[3
]}

Marder, Todd B. ^{[1
,2
]}

机构：

[1] Julius Maximilians Univ Wurzburg, Inst Inorgan Chem, D-97074 Wurzburg, Germany

[2] Julius Maximilians Univ Wurzburg, Inst Sustainable Chem & Catalysis Boron, D-97074 Wurzburg, Germany

[3] Julius Maximilians Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[4] Univ Ibadan, Fac Sci, Dept Chem, Ibadan 200284, Oyo, Nigeria

来源：

ACS CATALYSIS | 2016年 / 6卷 / 12期

关键词：

C-X activation; boron; cross-coupling; N-heterocyclic carbenes; Suzuki-Miyaura; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; COPPER-CATALYZED BORYLATION; CROSS-COUPLING REACTIONS; ALKOXY DIBORON REAGENTS; C-H BORYLATION; ARYL HALIDES; ALLYLIC SUBSTITUTION; CONJUGATE ADDITIONS; SECONDARY; TERTIARY;

D O I：

10.1021/acscatal.6b02918

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A copper(II)-catalyzed borylation of alkyl halides with bis(pinacolato)diboron (B(2)pin(2)) has been developed, which can be carried out in air, providing a wide range of primary, secondary, and some tertiary alkylboronates in high yields. A variety of functional groups are tolerated and the protocol is also applicable to unactivated alkyl chlorides (including 1,1- and 1,2-dichlorides). Preliminary mechanistic investigations show that this borylation reaction involves one-electron processes.

引用

页码：8332 / 8335

页数：4

共 66 条

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