Preparation of Polyfunctional Arylzinc Organometallics in Toluene by Halogen/Zinc Exchange Reactions

被引：28

作者：

Balkenhohl, Moritz ^{[1
]}

Ziegler, Dorothee S. ^{[1
]}

Desaintjean, Alexandre ^{[1
]}

Bole, Leonie J. ^{[3
]}

Kennedy, Alan R. ^{[3
]}

Hevia, Eva ^{[2
]}

Knochel, Paul ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany

[2] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

[3] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 37期

关键词：

alkoxides; lithium; metal; halogen exchange; organozinc reagents; toluene; ENHANCED AIR; CHEMOSELECTIVE METALATION; ZINC ORGANOMETALLICS; INSERTION; HALIDES; LICL; CHLORIDES; REAGENTS; KINETICS; COMPLEX;

D O I：

10.1002/anie.201906898

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A wide range of polyfunctional diaryl-and diheteroarylzinc species were prepared in toluene within 10 min to 5 h through an I/Zn or Br/Zn exchange reaction using bimetallic reagents of the general formula R2Zn center dot 2 LiOR (R=sBu, tBu, pTol). Highly sensitive functional groups, such as a triazine, a ketone, an aldehyde, or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of a plethora of functionalized (hetero)arenes after quenching with various electrophiles. Insight into the constitution and reactivity of these bimetallic mixtures revealed the formation of highly active lithium diorganodialkoxyzincates of type [R2Zn(OR)(2)Li-2].

引用

页码：12898 / 12902

页数：5

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