A Tutorial on Selectivity Determination in C(sp2)a 'H Oxidative Addition of Arenes by Transition Metal Complexes

Tyler P. Pabst; Paul J. Chirik

doi:10.1021/acs.organomet.1c00030

A Tutorial on Selectivity Determination in C(sp2)a 'H Oxidative Addition of Arenes by Transition Metal Complexes

Tyler P. Pabst, Paul J. Chirik

Chemistry

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

28 Scopus citations

Abstract

A Tutorial on factors that determine the selectivity in C(sp2)-H activation and functionalization reactions involving two-electron oxidative addition processes with transition metals is presented. The interplay of the thermodynamics of C(sp2)-H oxidative addition and kinetic influences upon regioselectivity are presented alongside pedagogically valuable experimental and computational results from the literature. Mechanisms and energetics of chelate-assisted C(sp2)-H oxidative addition are examined, as are concepts related to chemoselectivity in the oxidative addition of C(sp2)-H or C(sp2)-X (X = F, Cl, Br, I) bonds with aryl halide substrates.

Original language	English (US)
Pages (from-to)	813-831
Number of pages	19
Journal	Organometallics
Volume	40
Issue number	7
DOIs	https://doi.org/10.1021/acs.organomet.1c00030
State	Published - Apr 12 2021

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/acs.organomet.1c00030

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abstract = "A Tutorial on factors that determine the selectivity in C(sp2)-H activation and functionalization reactions involving two-electron oxidative addition processes with transition metals is presented. The interplay of the thermodynamics of C(sp2)-H oxidative addition and kinetic influences upon regioselectivity are presented alongside pedagogically valuable experimental and computational results from the literature. Mechanisms and energetics of chelate-assisted C(sp2)-H oxidative addition are examined, as are concepts related to chemoselectivity in the oxidative addition of C(sp2)-H or C(sp2)-X (X = F, Cl, Br, I) bonds with aryl halide substrates.",

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AB - A Tutorial on factors that determine the selectivity in C(sp2)-H activation and functionalization reactions involving two-electron oxidative addition processes with transition metals is presented. The interplay of the thermodynamics of C(sp2)-H oxidative addition and kinetic influences upon regioselectivity are presented alongside pedagogically valuable experimental and computational results from the literature. Mechanisms and energetics of chelate-assisted C(sp2)-H oxidative addition are examined, as are concepts related to chemoselectivity in the oxidative addition of C(sp2)-H or C(sp2)-X (X = F, Cl, Br, I) bonds with aryl halide substrates.

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A Tutorial on Selectivity Determination in C(sp2)a 'H Oxidative Addition of Arenes by Transition Metal Complexes

Abstract

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