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C–H Insertion via Ruthenium Catalyzed gem-Hydrogenation of 1,3-Enynes

Title	C–H Insertion via Ruthenium Catalyzed gem-Hydrogenation of 1,3-Enynes
Authors	Sebastian Peil, Alejandro Gutiérrez González, Markus Leutzsch, Alois Fürstner
Magazine	Journal of the American Chemical Society
Date	02/16/2022
DOI	https://doi.org/10.1021/jacs.1c13446
Introduction	The transformation of an internal alkyne through gem-hydrogenation using [Cp*RuCl] 4 as a precatalyst is a unique process. This method converts one carbon atom of a triple bond into a methylene group and the other into a ruthenium carbene. For 1,3-enynes with a propargylic steering substituent, the reaction is regioselective and results in vinyl carbene complexes displaying interconverting η1/η3-binding modes. These carbenes can insert into C–H bonds of the steering group or nearby ether, acetal, orthoester, or (sulfon)amide substituents. This reaction facilitates the synthesis of spirocyclic and bridged ring systems, vital for medicinal chemistry. The process is scalable and can produce deuterated isotopologues. PHIP NMR spectroscopy, in combination with labeling experiments, demonstrated that gem-hydrogenation initiates these reactions. Kinetic data shed light on the turnover-limiting transition state during the C–H insertion step.
Quote	Sebastian Peil, Alejandro Gutiérrez González and Markus Leutzsch et al. C–H Insertion via Ruthenium Catalyzed gem-Hydrogenation of 1,3-Enynes. J. Am. Chem. Soc. 2022. Vol. 144(9):4158-4167. DOI: 10.1021/jacs.1c13446
Element	Ruthenium (Ru) , Carbon (C) , Hydrogen (H)
Materials	Chemical Compounds
Industry	Chemical Manufacturing

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