Organoselenium and DMAP co-catalysis: regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes?

Chemical Communications Pub Date: 2016-02-15 DOI: 10.1039/C5CC10245F

Abstract

A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.

Graphical abstract: Organoselenium and DMAP co-catalysis: regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes
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