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

  • Lijun Fu
  • Xueli Mu
  • Baiqing Li
Original Paper


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.


Syn-dichlorination Diastereocontrol Organoselenium catalyst DFT calculation Reaction mechanism 



We would like to thank the National Natural Science Foundation for financial support.

Supplementary material

894_2018_3624_MOESM1_ESM.docx (47 kb)
ESM 1 (DOCX 46 kb)


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Institute of Theoretical Chemistry, School of Chemistry and Chemical Engineering and Key Laboratory of Colloid and Interface Chemistry (Ministry of Education)Shandong UniversityJinanPeople’s Republic of China

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