Flash Communication: N-Heterocyclic Carbene Nickel-Mediated C-C Activation of Substituted Vinylcyclobutanes

Cherish Nie; Marina Pérez-Jiménez; Junho Kim; Paul J. Chirik

doi:10.1021/acs.organomet.5c00130

Flash Communication: N-Heterocyclic Carbene Nickel-Mediated C-C Activation of Substituted Vinylcyclobutanes

Cherish Nie, Marina Pérez-Jiménez, Junho Kim, Paul J. Chirik

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The C-C activation of three substituted vinylcyclobutanes by [(IPr)Ni(0)] (IPr = ((1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) complexes was evaluated. Both 1,2-dicyclobutylethylene and β-caryophyllene underwent oxidative ring-opening with [(IPr)Ni(0)] to furnish isolable 7-membered alkyl, allyl-metallacycles at ambient temperature. In contrast, a derivative of β-caryophyllene bearing terminal alkenes resulted in formation of an isolable nickel bis(olefin) complex that exhibited only partial conversion to the metallacycle upon heating to 80 °C.

Original language	English (US)
Pages (from-to)	1134-1137
Number of pages	4
Journal	Organometallics
Volume	44
Issue number	11
DOIs	https://doi.org/10.1021/acs.organomet.5c00130
State	Published - Jun 9 2025

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/acs.organomet.5c00130

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abstract = "The C-C activation of three substituted vinylcyclobutanes by [(IPr)Ni(0)] (IPr = ((1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) complexes was evaluated. Both 1,2-dicyclobutylethylene and β-caryophyllene underwent oxidative ring-opening with [(IPr)Ni(0)] to furnish isolable 7-membered alkyl, allyl-metallacycles at ambient temperature. In contrast, a derivative of β-caryophyllene bearing terminal alkenes resulted in formation of an isolable nickel bis(olefin) complex that exhibited only partial conversion to the metallacycle upon heating to 80 °C.",

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T2 - N-Heterocyclic Carbene Nickel-Mediated C-C Activation of Substituted Vinylcyclobutanes

AU - Nie, Cherish

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AU - Kim, Junho

AU - Chirik, Paul J.

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AB - The C-C activation of three substituted vinylcyclobutanes by [(IPr)Ni(0)] (IPr = ((1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) complexes was evaluated. Both 1,2-dicyclobutylethylene and β-caryophyllene underwent oxidative ring-opening with [(IPr)Ni(0)] to furnish isolable 7-membered alkyl, allyl-metallacycles at ambient temperature. In contrast, a derivative of β-caryophyllene bearing terminal alkenes resulted in formation of an isolable nickel bis(olefin) complex that exhibited only partial conversion to the metallacycle upon heating to 80 °C.

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Flash Communication: N-Heterocyclic Carbene Nickel-Mediated C-C Activation of Substituted Vinylcyclobutanes

Abstract

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