Activation of Diazo Compounds by Fluorinated Triarylborane Catalysts

Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 and Pramanik, Milan 2023. Activation of Diazo Compounds by Fluorinated Triarylborane Catalysts. Synthesis: Journal of Synthetic Organic Chemistry 10.1055/a-2118-3046

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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.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Publisher:	Thieme Gruppe
ISSN:	0039-7881
Funders:	EPSRC
Date of First Compliant Deposit:	27 July 2023
Date of Acceptance:	26 June 2023
Last Modified:	16 Sep 2023 00:27
URI:	https://orca.cardiff.ac.uk/id/eprint/161314

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