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Triarylborane catalyzed carbene transfer reactions using diazo precursors

Dasgupta, Ayan, Richards, Emma and Melen, Rebecca L. 2021. Triarylborane catalyzed carbene transfer reactions using diazo precursors. ACS Catalysis 12 , 442–452. 10.1021/acscatal.1c04746

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Abstract

Reactive carbenes generated from diazo compounds are key intermediates for a range of organic reactions to afford synthetically useful organic compounds. The majority of these reactions have been carried out using transition metal catalysts. However, the formation of carbene intermediates using main group elements has not been widely investigated for synthetic purposes. Recent studies have demonstrated that triarylboranes can be used for the in situ generation of reactive carbene intermediates in both stoichiometric and catalytic reactions. These new reactivities of triarylboranes have gained significant attention in synthetic chemistry particularly in catalytic studies. The range of organic compounds that have been synthesized through these reactions are important as pharmaceuticals or agrochemicals. In this perspective, we highlight the recent progress and ongoing challenges of carbene transfer reactions generated from their corresponding diazo precursors using triarylboranes as catalysts. We also highlight the stoichiometric use of triarylboranes in which the boranes not only activate the diazo functionality to afford a carbene intermediate but also actively participate in the reactions as a reagent. The different mechanisms for activation and carbene transfer are described along with the mechanistic and computational studies that have aided the elucidation of these reaction pathways. Potential opportunities for the use of boranes as a catalyst toward different carbene transfer reactions and their future prospects are discussed.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: American Chemical Society
ISSN: 2155-5435
Funders: EPSRC and Leverhulme Trust
Date of First Compliant Deposit: 22 December 2021
Date of Acceptance: 1 December 2021
Last Modified: 31 Jan 2022 08:50
URI: https://orca.cardiff.ac.uk/id/eprint/146282

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