Synlett 2019; 30(10): 1105-1110
DOI: 10.1055/s-0037-1611728
synpacts
© Georg Thieme Verlag Stuttgart · New York

Deoxygenative Transformation of Carbonyl and Carboxyl Compounds Using gem-Diborylalkanes

Yue Hu
a  State 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
a  State 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
b  University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
a  State 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
› Author Affiliations

This work was supported by the National Natural Science Foundation of China (Grant no. 91745110, 21673261, 21603245, 21633013, 21703265, 21872156 and 21802150), Natural Science Foundation of Jiangsu Province (Grant no. BK20181194, BK20180247), and a start-up funding from LICP. Support from the Young Elite Scientist Sponsorship Program by CAST, the Youth Innovation Promotion Association CAS (2018458).
Further Information

Publication History

Received: 10 January 2019

Accepted after revision: 23 January 2019

Publication Date:
21 February 2019 (online)

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

 
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