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

Research output: Contribution to journalArticle

22 Citations (Scopus)

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
StatePublished - Aug 26 2013

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Alkynes
Alkenes
alkynes
Catalysis
alkenes
catalysis
switches
selectivity
Switches
rings
products
Discrete Fourier transforms
catalysts
Catalysts

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Mo, Dong Liang ; Chen, Bo ; Ding, Chang Hua ; Dai, Li Xin ; Ge, Guang Cun ; Hou, Xue Long. / Switch of addition and ring-opening reactions of oxabicyclic alkenes with terminal alkynes by sp2-C,P- and sp3-C,P-Palladacycle catalysis. In: Organometallics. 2013 ; Vol. 32, No. 16. pp. 4465-4468.
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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.",
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Switch of addition and ring-opening reactions of oxabicyclic alkenes with terminal alkynes by sp2-C,P- and sp3-C,P-Palladacycle catalysis. / Mo, Dong Liang; Chen, Bo; Ding, Chang Hua; Dai, Li Xin; Ge, Guang Cun; Hou, Xue Long.

In: Organometallics, Vol. 32, No. 16, 26.08.2013, p. 4465-4468.

Research output: Contribution to journalArticle

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AU - Dai, Li Xin

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AU - Hou, Xue Long

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AB - 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.

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