Mechanism of Ni-Catalyzed Photochemical Halogen Atom-Mediated C(sp3)–H Arylation

Cusumano, Alexander Q.; Chaffin, Braden C.; Doyle, Abigail G.

doi:10.1021/jacs.4c03099

Mechanism of Ni-Catalyzed Photochemical Halogen Atom-Mediated C(sp³)–H Arylation

Journal Article · Wed May 22 00:00:00 EDT 2024 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.4c03099· OSTI ID:2426918

Cusumano, Alexander Q. ^[1]; Chaffin, Braden C. ^[2]; ^[2]

University of California, Los Angeles, CA (United States); University of California, Los Angeles
University of California, Los Angeles, CA (United States)

Within the context of Ni photoredox catalysis, halogen atom photoelimination from Ni has emerged as a fruitful strategy for enabling hydrogen atom transfer (HAT)-mediated C(sp³)–H functionalization. Despite the numerous synthetic transformations invoking this paradigm, a unified mechanistic hypothesis that is consistent with experimental findings on the catalytic systems and accounts for halogen radical formation and facile C(sp²)–C(sp³) bond formation remains elusive. We employ kinetic analysis, organometallic synthesis, and computational investigations to decipher the mechanism of a prototypical Ni-catalyzed photochemical C(sp³)–H arylation reaction. Our findings revise the previous mechanistic proposals, first by examining the relevance of SET and EnT processes from Ni intermediates relevant to the HAT-based arylation reaction. Our investigation highlights the ability for blue light to promote efficient Ni–C(sp²) bond homolysis from cationic Ni^III and C(sp²)–C(sp³) reductive elimination from bipyridine Ni^II complexes. However interesting, the rates and selectivities of these processes do not account for the productive catalytic pathway. Instead, our studies support a mechanism that involves halogen atom evolution from in situ generated Ni^II dihalide intermediates, radical capture by a Ni^II(aryl)(halide) resting state, and key C–C bond formation from Ni^III. Oxidative addition to Ni^I, as opposed to Ni⁰, and rapid Ni^III/Ni^I comproportionation play key roles in this process. Furthermore, the findings presented herein offer fundamental insight into the reactivity of Ni in the broader context of catalysis.

View Accepted Manuscript (DOE)

Research Organization:: University of California, Los Angeles, CA (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0019370

OSTI ID:: 2426918

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 22 Vol. 146; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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