Issue 22, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
13 Dec 2015
Accepted
09 Feb 2016
First published
15 Feb 2016

Chem. Commun., 2016,52, 4179-4182

Author version available

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

A. Verma, S. Jana, Ch. Durga Prasad, A. Yadav and S. Kumar, Chem. Commun., 2016, 52, 4179 DOI: 10.1039/C5CC10245F

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