Mechanism of Cu-catalyzed iododeboronation : a description of ligand-enabled transmetalation, disproportionation, and turnover in Cu-mediated oxidative coupling reactions
Date
18/08/2023Author
Grant ID
BB/R013780/1
EP/R025754/1
EP/W007517/1
EP/S027165/1
RF-2022-014
Keywords
Metadata
Show full item recordAbstract
We report a combined experimental and computational study of the mechanism of the Cu-catalyzed arylboronic acid iododeboronation reaction. A combination of structural and density functional theory (DFT) analyses has allowed determination of the identity of the reaction precatalyst with insight into each step of the catalytic cycle. Key findings include a rationale for ligand (phen) stoichiometry related to key turnover events─the ligand facilitates transmetalation via H-bonding to an organoboron boronate generated in situ and phen loss/gain is integral to the key oxidative events. These data provide a framework for understanding ligand effects on these key mechanistic processes, which underpin several classes of Cu-mediated oxidative coupling reactions.
Citation
Andrews , M , Charpentier , A , Slawin , A M Z , Cordes , D B , Macgregor , S & Watson , A J B 2023 , ' Mechanism of Cu-catalyzed iododeboronation : a description of ligand-enabled transmetalation, disproportionation, and turnover in Cu-mediated oxidative coupling reactions ' , ACS Catalysis , vol. 13 , no. 16 , pp. 11117-11126 . https://doi.org/10.1021/acscatal.3c02839
Publication
ACS Catalysis
Status
Peer reviewed
ISSN
2155-5435Type
Journal article
Description
Funding: Biotechnology and Biological Sciences Research Council - BB/R013780/; Engineering and Physical Sciences Research Council - EP/R025754/1, EP/W007517/1, EP/S027165/1; Leverhulme Trust - RF-2022-014.Collections
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