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Remote Allylation of Unactivated C(sp³)-H Bonds Triggered by Photogenerated Amidyl Radicals.

ABSTRACT: The allylation reaction is a highly versatile transformation in chemical synthesis. While many elegant direct C(sp²)-H allylation reactions have been developed, the direct allylation of unactivated C(sp³)-H bonds is underdeveloped. By applying photoredox catalysis and a [1,5]-HAT process, herein we report a direct allylation of unactivated C(sp³)‒H bonds. This photocatalyzed transformation is tolerant of several functional groups in the amide and allylic chloride substrates. Various allyl-substituted amide products were obtained with good yields and high δ-selectivity.

SUBMITTER: Xu B

PROVIDER: S-EPMC8186322 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Remote Allylation of Unactivated C(sp3)-H Bonds Triggered by Photogenerated Amidyl Radicals.

Xu Bin B Tambar Uttam K UK

ACS catalysis 20190416 5

The allylation reaction is a highly versatile transformation in chemical synthesis. While many elegant direct C(sp2)-H allylation reactions have been developed, the direct allylation of unactivated C(sp3)-H bonds is underdeveloped. By applying photoredox catalysis and a [1,5]-HAT process, herein we report a direct allylation of unactivated C(sp3)‒H bonds. This photocatalyzed transformation is tolerant of several functional groups in the amide and allylic chloride ...[more]

PMID: 34109055

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