Mechanistic Investigation of the Rhodium-Catalysed Transfer Hydroarylation Reaction Involving Reversible C–C Bond Activation

Title	Mechanistic Investigation of the Rhodium-Catalysed Transfer Hydroarylation Reaction Involving Reversible C–C Bond Activation
Authors	Marius D. R. Lutz, Sven Roediger, Miguel A. Rivero-Crespo, Bill Morandi
Magazine	Journal of the American Chemical Society
Date	11/30/2023
DOI	10.1021/jacs.3c07780
Introduction	The activation of carbon–carbon (C–C) bonds, typically considered unreactive, has gained attention for its potential to reshape small molecule frameworks directly. Traditional methods are often limited to strained molecules or require directing groups, but here, we present a mechanistic analysis of a unique rhodium-catalysed C–C bond cleavage in unstrained alcohols. This process allows for reversible ketone transfer hydroarylation, with insights gained from kinetic studies, in situ NMR, and DFT calculations. These findings highlight a symmetric catalytic cycle featuring a reversible β-carbon elimination. Our study identifies the turnover-limiting step, the resting state of the catalyst, and the impact of the bulky NHC ligand. Furthermore, we identified two air-stable precatalysts that enhance catalytic activity compared to previous methods.
Quote	Marius D. R. Lutz, Sven Roediger and Miguel A. Rivero-Crespo et al. Mechanistic Investigation of the Rhodium-Catalysed Transfer Hydroarylation Reaction Involving Reversible C–C Bond Activation. J. Chem. Soc. 2023. DOI: 10.1021/jacs.3c07780
Element	Carbon (C) , Rhodium (Rh)
Industry	Chemical & Pharmacy

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