Deoxygenative Transformation of Carbonyl and Carboxyl Compounds Using gem-Diborylalkanes

Yue Hu; Wei Sun; Chao Liu

doi:10.1055/s-0037-1611728

Synlett, Table of Contents

Synlett 2019; 30(10): 1105-1110
DOI: 10.1055/s-0037-1611728

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Deoxygenative Transformation of Carbonyl and Carboxyl Compounds Using gem-Diborylalkanes

Yue Hu

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China Email: chaoliu@licp.cas.cn

,

Wei Sun

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China Email: chaoliu@licp.cas.cn

^bUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Chao Liu *

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China Email: chaoliu@licp.cas.cn

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Abstract

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Abstract

gem-Diborylalkanes serve as privileged carbanion precursors for the efficient construction of carbon–carbon bond with various carbonyl and carboxyl compounds. We highlight the recent advances on deoxygenative transformation of carbonyl and carboxyl compounds using gem-diborylalkanes reagents. Our recent development of a dual functionalization of gem-diborylalkanes through deoxygenative enolization with the carboxylic acids is also discussed.

1 Introduction

2 Activation Modes of gem-Diborylalkanes

3 Deoxygenative Transformation of Carbonyl and Carboxyl Compounds via α-Diboryl Carbanion

3.1 Reaction with Aldehyde and Ketone Electrophiles

3.2 Reaction with Carboxylic Acid Derivatives

4 Deoxygenative Transformation of Carbonyl and Carboxyl Compounds via α-Monoboryl Carbanion

5 Conclusion

Key words

gem-diborylalkanes - carbonyl compounds - carboxylic acids - deoxygenative - carbanion - electrophiles

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References

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