Two-State Reactivity in Iron-Catalyzed Alkene Isomerization Confers σ-Base Resistance | Zendy

Sean A. Lutz | Zendy; Anne K. Hickey | Zendy; Yafei Gao | Zendy; ChunHsing Chen | Zendy; Jeremy M. Smith | Zendy

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Two-State Reactivity in Iron-Catalyzed Alkene Isomerization Confers σ-Base Resistance

Author(s) -

Sean A. Lutz,

Anne K. Hickey,

Yafei Gao,

ChunHsing Chen,

Jeremy M. Smith

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c07300

Subject(s) - chemistry , isomerization , alkene , catalysis , reactivity (psychology) , photochemistry , substrate (aquarium) , organic chemistry , medicine , oceanography , alternative medicine , pathology , geology

A low-coordinate, high spin ( S = 3/2) organometallic iron(I) complex is a catalyst for the isomerization of alkenes. A combination of experimental and computational mechanistic studies supports a mechanism in which alkene isomerization occurs by the allyl mechanism. Importantly, while substrate binding occurs on the S = 3/2 surface, oxidative addition to an η 1 -allyl intermediate only occurs on the S = 1/2 surface. Since this spin state change is only possible when the alkene substrate is bound, the catalyst has high immunity to typical σ-base poisons due to the antibonding interactions of the high spin state.

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