Switch of addition and ring-opening reactions of oxabicyclic alkenes with terminal alkynes by sp2-C,P- and sp3-C,P-Palladacycle catalysis

Dong Liang Mo, Bo Chen, Chang Hua Ding, Li Xin Dai, Guang Cun Ge, Xue Long Hou

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Abstract

Palladacycles were found to be efficient catalysts for the reaction of oxabicyclic alkenes with terminal alkynes. A switch of reaction selectivity was realized using a palladacycle with an sp2 or sp3 C-Pd bond. Addition products were afforded predominantly using a palladacycle with an sp3 C-Pd bond, while ring-opening compounds were the major products when palladacycles having an sp2 C-Pd bond were used. DFT calculations revealed that the different trans effects of the sp2-C and sp3-C donors in palladacycles are responsible for the switch in selectivity.

Original languageEnglish (US)
Pages (from-to)4465-4468
Number of pages4
JournalOrganometallics
Volume32
Issue number16
DOIs
Publication statusPublished - Aug 26 2013

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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