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Issue 22, 2016
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Organoselenium and DMAP co-catalysis: regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes

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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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The article was received on 13 Dec 2015, accepted on 09 Feb 2016 and first published on 15 Feb 2016


Article type: Communication
DOI: 10.1039/C5CC10245F
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Citation: Chem. Commun., 2016,52, 4179-4182
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    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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