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PtI2-catalyzed cyclization of 3-acyloxy-1,5-enynes with the elimination of HOAc and a benzyl shift: synthesis of unsymmetrical m-terphenyls.

Authors
  • Huang, Kaimeng
  • Ke, Xiaona
  • Wang, Hongkai
  • Wang, Junying
  • Zhou, Chenchen
  • Xu, Xiufang
  • Liu, Lingyan
  • Li, Jing
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Apr 21, 2015
Volume
13
Issue
15
Pages
4486–4493
Identifiers
DOI: 10.1039/c4ob02336f
PMID: 25772066
Source
Medline
License
Unknown

Abstract

A novel cyclization of 3-acyloxy-1,5-enynes is developed in the presence of PtI2 for the synthesis of substituted unsymmetrical m-terphenyls in good to excellent yields. Two unique steps are involved in this transformation, which includes the elimination of HOAc and benzyl group migration. DFT calculations indicated that the rate-determining step is the migration of the benzylic carbocation to form a zwitterionic intermediate followed by the elimination of HOAc. The subsequent cyclopropanation of the zwitterionic intermediate is the regioselectivity-determining step.

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