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Visible-light-mediated Minisci C-H alkylation of heteroarenes with unactivated alkyl halides using O₂ as an oxidant.

ABSTRACT: Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature. This mild protocol is compatible with a wide array of sensitive functional groups and has a broad substrate scope. Notably, functionalization of (iso)quinolines, pyridines, phenanthrolines, quinazoline, and other heterocyclic compounds with unactivated primary, secondary, and tertiary alkyl halides proceeds smoothly under the standard conditions. The robustness of this protocol is further demonstrated by the late-stage functionalization of complex nitrogen-containing natural products and drugs.

SUBMITTER: Dong J

PROVIDER: S-EPMC6349069 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Visible-light-mediated Minisci C-H alkylation of heteroarenes with unactivated alkyl halides using O2 as an oxidant.

Dong Jianyang J Lyu Xueli X Wang Zhen Z Wang Xiaochen X Song Hongjian H Liu Yuxiu Y Wang Qingmin Q

Chemical science 20181127 4

Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature. This mild protocol is compatible with a wide array of sensitive functional groups and has a broad substrate scope. Notably, functionalization of (iso)quinolines, pyridines, phenanthrolines, quinazoline, and other heterocyclic compounds with unactivated primary, secondary, and tertiary alkyl halides proceeds ...[more]

PMID: 30774891

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