Regio‐ and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H‐Pyrans: Heck Coupling of Monocyclopropanated Heterocycles

Heck‐type arylation of cyclopropanated furans and pyrroles proceeds with ring expansion via the unactivated cyclopropyl bond, giving rise to arylated diyhdropyridines, pyridines, and 2H‐pyrans.

Abstract

A palladium‐catalyzed coupling between aryl halides and monocyclopropanated pyrroles or furans has been developed, leading to valuable six‐membered N‐ and O‐heterocycles. As the key step, a selective cleavage of the non‐activated endocyclic C−C bond of the 2‐heterobicyclo‐[3.1.0]hexane framework is achieved. The developed method offers access to highly functionalized piperidines, pyridines, and pyrans that are challenging to access by traditional methods.

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