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

doi:10.1021/om400653x

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

Chemistry

Research output: Contribution to journal › Article

24 Scopus citations

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 language	English (US)
Pages (from-to)	4465-4468
Number of pages	4
Journal	Organometallics
Volume	32
Issue number	16
DOIs	https://doi.org/10.1021/om400653x
Publication status	Published - Aug 26 2013

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All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Cite this

Mo, D. L., Chen, B., Ding, C. H., Dai, L. X., Ge, G. C., & Hou, X. L. (2013). Switch of addition and ring-opening reactions of oxabicyclic alkenes with terminal alkynes by sp²-C,P- and sp³-C,P-Palladacycle catalysis. Organometallics, 32(16), 4465-4468. https://doi.org/10.1021/om400653x

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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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AU - Ge, Guang Cun

AU - Hou, Xue Long

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10.1021/om400653x