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Radical ?-C-H Cyclobutylation of Aniline Derivatives.

ABSTRACT: A catalytic system has been developed for the direct alkylation of ?-C-H bonds of aniline derivatives with strained C-C ?-bonds. This method operates through a photoredox mechanism in which oxidative formation of aminoalkyl radical intermediates enables addition to a bicyclobutane derivative, giving rise to ?-cyclobutyl N-alkylaniline products. This mild system proceeds through a redox- and proton-neutral mechanism and is operational for a range of substituted arylamine derivatives.

SUBMITTER: Pratt CJ

PROVIDER: S-EPMC7043791 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Radical α-C-H Cyclobutylation of Aniline Derivatives.

Pratt Cameron J CJ Aycock R Adam RA King Max D MD Jui Nathan T NT

Synlett : accounts and rapid communications in synthetic organic chemistry 20190903 1

A catalytic system has been developed for the direct alkylation of α-C-H bonds of aniline derivatives with strained C-C σ-bonds. This method operates through a photoredox mechanism in which oxidative formation of aminoalkyl radical intermediates enables addition to a bicyclobutane derivative, giving rise to α-cyclobutyl <i>N</i>-alkylaniline products. This mild system proceeds through a redox- and proton-neutral mechanism and is operational for a range of substituted arylamine derivatives. ...[more]

PMID: 32103861

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