Synlett 2020; 31(10): 933-937
DOI: 10.1055/s-0039-1690811
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© Georg Thieme Verlag Stuttgart · New York

A Frustrated Lewis Pair Solution to a Frustrating Problem: Mono-Selective Functionalization of C–F Bonds in Di- and Trifluoromethyl Groups

Richa Gupta
,
Amit K. Jaiswal
,
Dipendu Mandal
,
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore   Email: rowan.young@nus.edu.sg
› Author Affiliations
We thank the Singapore Ministry of Education (R-143-000-A05-112) and the Singapore Agency of Science, Technology and Research (A*STAR) (R-143-000-B09-305) for funding.
Further Information

Publication History

Received: 11 December 2019

Accepted after revision: 15 January 2020

Publication Date:
28 January 2020 (online)


Abstract

Polyfluoromethyl groups generally suffer from over-reaction, where multiple C–F bonds are uncontrollably functionalized. The use of a frustrated Lewis pair (FLP)-mediated C–F bond activation permits selective monodefluorination through base capture of intermediate fluorocarbocations. FLP-mediated C–F bond activation can be applied to aromatic, heteroaromatic, or nonaromatic difluoro and trifluoromethyl groups to generate selectively fluoride-substituted phosphonium and pyridinium salts. These salts can be further functionalized by Wittig coupling, nucleophilic substitution, photoredox alkylation, nucleophilic transfer, or hydrogenation reactions to install a range of functional groups into the activated C–F position.

1 Introduction

2 Frustrated Lewis Pair C–F Activation

3 Conclusion

 
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