Recent Advances in the Synthetic Application of Difluorocarbene

Chuanfa Ni; Jinbo Hu

doi:10.1055/s-0033-1340856

Synthesis, Table of Contents

Synthesis 2014; 46(07): 842-863
DOI: 10.1055/s-0033-1340856

review

Recent Advances in the Synthetic Application of Difluorocarbene

Chuanfa Ni

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, P. R. of China Fax: +86(21)64166128 Email: jinbohu@sioc.ac.cn

,

Jinbo Hu*

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032, P. R. of China Fax: +86(21)64166128 Email: jinbohu@sioc.ac.cn

› Author Affiliations

Abstract

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Abstract

Difluorocarbene is a versatile, reactive intermediate for use in organic synthesis. Over the past decade, significant progress has been made in difluorocarbene chemistry owing to the increasing demand for various fluorinated molecules. Not only the substrate scope for some classical difluorocarbene reagents has been largely expanded, but also new and environmentally friendly difluorocarbene reagents for difluoromethylation and gem-difluorocyclization have been developed. This review summarizes the difluoromethylation, gem-difluorocyclopropanation, gem-difluorocyclopropenation, gem-difluoroolefination, and trifluoromethylation achieved in the last decade using both the classical and the new difluorocarbene sources.

1 Introduction

2 Difluorocarbene Sources

3 Difluoromethylation

3.1 O-Difluoromethylation

3.2 S-Difluoromethylation

3.3 N-Difluoromethylation

3.4 Difluoromethylation of Ambident N,O- and N,S-Nucleophiles

3.5 Se- and P-Difluoromethylation

3.6 C-Difluoromethylation

3.7 Sn-Difluoromethylation

4 gem-Difluorocyclization

4.1 gem-Difluorocyclopropanation

4.2 gem-Difluorocyclopropenation

5 gem-Difluoroolefination and Related Reactions

6 Trifluoromethylation

7 Miscellaneous

8 Conclusions

Key words

difluorocarbene - difluoromethylation - cycloaddition - gem-difluoroolefination - trifluoromethylation

Full Text

References

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