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C(sp²)-H Hydroxylation via Catalytic 1,4-Ni Migration with N₂O.

ABSTRACT: Herein, we report a Ni-catalyzed C(sp²)-H hydroxylation of aryl bromides with N₂O as an oxygen-atom donor. The reaction is enabled by a 1,4-Ni translocation that results in ipso/ortho difunctionalized products. Regioselectivity and stereocontrol are dictated by a judicious choice of the ligand backbone, thus giving access to either carbonyl or phenol derivatives and offering an opportunity to repurpose hazardous substances en route to valuable oxygen-containing building blocks.

SUBMITTER: Zhang H

PROVIDER: S-EPMC10586377 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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C(sp2)-H Hydroxylation via Catalytic 1,4-Ni Migration with N2O.

Zhang Huihui H Rodrigalvarez Jesus J Martin Ruben R

Journal of the American Chemical Society 20230802 32

Herein, we report a Ni-catalyzed C(sp2)-H hydroxylation of aryl bromides with N2O as an oxygen-atom donor. The reaction is enabled by a 1,4-Ni translocation that results in ipso/ortho difunctionalized products. Regioselectivity and stereocontrol are dictated by a judicious choice of the ligand backbone, thus giving access to either carbonyl or phenol derivatives and offering an opportunity to repurpose hazardous substances en route to valuable oxygen-containing build ...[more]

PMID: 37531410

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