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 › peer-review

25 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
State	Published - Aug 26 2013

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/om400653x

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

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.",

author = "Mo, {Dong Liang} and Bo Chen and Ding, {Chang Hua} and Dai, {Li Xin} and Ge, {Guang Cun} and Hou, {Xue Long}",

year = "2013",

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doi = "10.1021/om400653x",

language = "English (US)",

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T1 - Switch of addition and ring-opening reactions of oxabicyclic alkenes with terminal alkynes by sp2-C,P- and sp3-C,P-Palladacycle catalysis

AU - Mo, Dong Liang

AU - Chen, Bo

AU - Ding, Chang Hua

AU - Dai, Li Xin

AU - Ge, Guang Cun

AU - Hou, Xue Long

PY - 2013/8/26

Y1 - 2013/8/26

N2 - 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.

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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