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DOI: 10.1055/a-2118-3046
Activation of Diazo Compounds by Fluorinated Triarylborane Catalysts
The authors would like to thank the Engineering and Physical Sciences Research Council (EPSRC) for funding (EP/R026912/1).
Abstract
The diverse applicability of diazo compounds as versatile reagents has enlarged the chemical toolbox in organic synthesis. Over the past few decades, transition-metal-catalyzed diazo compound activation has ignited the classical synthetic methodology via utilizing highly reactive metal carbenoid species. Many reviews have also appeared in the literature that show the advantages and disadvantages of metal-catalyzed activation of diazo compounds. Recently, tris(pentafluorophenyl)borane-mediated diazo activation reactions has remodeled this research area due to the potential for mild, environmentally friendly, metal-free, nontoxic reaction conditions, and the diverse reactivity patterns of boranes towards diazo compounds. In this review, we discuss the reactivity of the boron–diazo precursor adducts with compounds using catalytic and stoichiometric halogenated triarylboranes and, the mechanism of N2 release from the diazo reagent. This generates the reactive carbene species as a key intermediate which can further be exploited for O–H, N–H, S–H, and C–H insertions, azide insertion, carbonate transfer, C–C and C=C bond forming reactions, [2+2] or [2+4] cascade cyclization reactions, annulation reactions, etc.
1 Introduction
2 Diazo Activation Using Stoichiometric Boranes
3 Diazo Activation Using Catalytic B(C6F5)3
4 B(C6F5)3-Catalyzed Diazo Activation Reactions
5 Conclusions
Publication History
Received: 31 May 2023
Accepted after revision: 26 June 2023
Accepted Manuscript online:
27 June 2023
Article published online:
26 July 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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