3 years ago

Fused-Ring Formation via an Intramolecular "Cut-and-Sew" Reaction between Cyclobutanones and Alkynes

Guangbin Dong, Lin Deng, Likun Jin
Herein, we describe the development of a catalytic intramolecular "cut-and-sew" transformation between cyclobutanones and alkynes to construct cyclohexenone-fused rings. The challenge arises from the need for selective coupling at the more sterically hindered proximal position, which can be addressed using an electron-rich but less bulky phosphine ligand. The control experiment and 13C-labelling study suggest that the reaction may start with cleavage of the less hindered distal C-C bond of cyclobutanones, followed by decarbonylation and CO reinsertion to enable Rh insertion at the more hindered proximal position.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201712487

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