Anti-Markovnikov hydro(amino)alkylation of vinylarenes via photoredox catalysis

Zhao Wu, Samuel N. Gockel and Kami L. Hull ()
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Zhao Wu: University of Illinois at Urbana-Champaign
Samuel N. Gockel: University of Illinois at Urbana-Champaign
Kami L. Hull: University of Texas at Austin

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Photoredox catalysis is a powerful means to generate odd-electron species under mild reaction conditions from a wide array of radical precursors. Herein, we present the application of this powerful catalytic manifold to address the hydroalkylation and hydroaminoalkylation of electronically diverse vinylarenes. This reaction allows for generalized alkene hydroalkylation leveraging common alkyl radical precursors, such as organotrifluoroborate salts and carboxylic acids. Furthermore, utilizing easily accessible α-silyl amine reagents or tertiary amines directly, secondary and tertiary amine moieties can be installed onto monoaryl and diaryl alkenes to access valuable products, including γ,γ-diarylamines pharmacophores. Thus, under a unified system, both hydroalkylation and hydroaminoalkylation of alkenes are achieved. The substrate scope is evaluated through 57 examples, the synthetic utility of the method is demonstrated, and preliminary mechanistic insights are presented.

Date: 2021
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DOI: 10.1038/s41467-021-26170-6

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