Reaction mechanism of organoselenium-catalyzed syn-dichlorination of alkenes: a DFT study

Reaction mechanism of organoselenium-catalyzed syn-dichlorination of alkenes: a DFT study A new method for the syn-dichlorination of alkenes at room temperature has been proposed by Denmark et al. The method uses diselenide (PhSeSePh) as the precatalyst, benzyltriethylammonium chloride (BnEt3NCl) as the source of chlorine, and an N-fluoropyridinium salt as the oxidant to recover the catalyst. This approach has achieved exquisite diastereocontrol on a number of alkene substrates. In this paper, we report the results of DFT calculations we performed to study the mechanism of this reaction. We were able to identify a reasonable reaction path, including the intermediate and transition-state structures. The results also indicate that PhSeCl3, rather than PhSeCl, is the active catalyst. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Molecular Modeling Springer Journals

Reaction mechanism of organoselenium-catalyzed syn-dichlorination of alkenes: a DFT study

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Publisher
Springer Berlin Heidelberg
Copyright
Copyright © 2018 by Springer-Verlag GmbH Germany, part of Springer Nature
Subject
Chemistry; Computer Applications in Chemistry; Molecular Medicine; Computer Appl. in Life Sciences; Characterization and Evaluation of Materials; Theoretical and Computational Chemistry
ISSN
1610-2940
eISSN
0948-5023
D.O.I.
10.1007/s00894-018-3624-9
Publisher site
See Article on Publisher Site

Abstract

A new method for the syn-dichlorination of alkenes at room temperature has been proposed by Denmark et al. The method uses diselenide (PhSeSePh) as the precatalyst, benzyltriethylammonium chloride (BnEt3NCl) as the source of chlorine, and an N-fluoropyridinium salt as the oxidant to recover the catalyst. This approach has achieved exquisite diastereocontrol on a number of alkene substrates. In this paper, we report the results of DFT calculations we performed to study the mechanism of this reaction. We were able to identify a reasonable reaction path, including the intermediate and transition-state structures. The results also indicate that PhSeCl3, rather than PhSeCl, is the active catalyst.

Journal

Journal of Molecular ModelingSpringer Journals

Published: Mar 13, 2018

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