Synthesis 2021; 53(24): 4599-4613
DOI: 10.1055/a-1561-7953
short review

Boron Lewis Pair Mediated C–H Activation and Borylation

Frédéric-Georges Fontaine
,
Vincent Desrosiers
V.D. acknowledges the Fonds de recherche du Québec - Nature et Technologies (FRQNT) and the Natural Sciences and Engineering Research Council (NSERC) for scholarships. F.-G.F. thanks NSERC for a Canada Research Chair. This work was supported by the Natural Sciences and Engineering Research Council (NSERC) of Canada and the Centre de Catalyse et Chimie Verte (Québec).


§ Canada Research Chair in Green Catalysis and Metal-Free Processes

Abstract

In the few past years, the chemistry of frustrated Lewis pairs (FLP) has enabled a plethora of transformations that would otherwise only be possible using transition metal catalysts. Of particular interest are C–H bond activation and borylation reactions, which are the subject of this review. The FLP borylation chemistry is compared with the early borylation methodologies using strongly electrophilic borenium ions. We present the mechanism of the C–H borylation using inter- and intramolecular Lewis pairs, along with some applications of these transformations.

1 Introduction

2 Electrophilic Borylation

3 Intramolecular or Directed Electrophilic Borylation

4 Intermolecular FLP-Mediated C–H Borylation

5 Stoichiometric Borylation by Intramolecular FLPs

5.1 Csp–H Borylation

5.2 Csp2–H Borylation

5.3 Csp3–H Borylation

6 Catalytic Borylation by Intramolecular FLPs

7 Catalytic Borylation by Self-Assembled FLPs

8 Conclusion



Publication History

Received: 30 June 2021

Accepted after revision: 29 July 2021

Publication Date:
29 July 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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