Reaction of Diazo Compounds with Organoboron Compounds

Huan Li; Yan Zhang; Jianbo Wang

doi:10.1055/s-0033-1340041

Synthesis, Table of Contents

Synthesis 2013; 45(22): 3090-3098
DOI: 10.1055/s-0033-1340041

short review

Reaction of Diazo Compounds with Organoboron Compounds

Authors

Huan Li

Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China Fax: +86(10)62751708 Email: wangjb@pku.edu.cn
Yan Zhang

Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China Fax: +86(10)62751708 Email: wangjb@pku.edu.cn
Jianbo Wang*

Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China Fax: +86(10)62751708 Email: wangjb@pku.edu.cn

Abstract

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Dedicated to Professor Guoqiang Lin

Abstract

The transition-metal-free reactions of diazo compounds with organoboron compounds are reviewed. This type of reaction provides an alternative approach for the formation of C–C, C–B, and C–Si bonds. Moreover, by using tosylhydrazones as diazo compound precursors and boronic acids/esters as the boron substrates, this type of reaction becomes of practical use in organic synthesis. This short review covers the recent developments of this area with an introduction to the historical background.

1 Introduction

2 Reaction of Diazo Compounds with Organoboranes

3 Reactions of Diazo Compounds with Boronic Acids and Related Organoborons

4 Reaction of Diazo Compounds with Boronic Esters

5 Concluding Remarks

Key words

diazo compounds - boron - hydrazine - transition-metal-free reactions - 1,2-migration

Full Text

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