Photoredox-Catalyzed\nMarkovnikov Hydroamination of\nAlkenes with Azoles

A visible-light induced intermolecular\nhydroamination\nof alkenes\nwith azoles is reported, delivering pharmaceutically valuable N-benzyl\nazoles in high yields with excellent Markovnikov selectivity. Mechanistic\nstudies suggest that the process is initiated by the energy transfer\nof the excited photocatalyst with alkenes, followed by the single\nelectron reduction, protonation, and subsequent single electron oxidation\nto afford the key alkyl carbocation intermediate. This protocol exhibits\nadvantages of broad functional group tolerance, excellent atom economy,\nhigh efficiency, and mild reaction conditions.

Publication Details

Journal
Figshare
Published
2024-10-30
DOI
https://doi.org/10.1021/acs.orglett.4c03418.s001
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Libraries and Information Services
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article
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article

Photoredox-Catalyzed\nMarkovnikov Hydroamination of\nAlkenes with Azoles

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Libraries and Information Services
article

Photoredox-Catalyzed\nMarkovnikov Hydroamination of\nAlkenes with Azoles

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Abstract

A visible-light induced intermolecular\nhydroamination\nof alkenes\nwith azoles is reported, delivering pharmaceutically valuable N-benzyl\nazoles in high yields with excellent Markovnikov selectivity. Mechanistic\nstudies suggest that the process is initiated by the energy transfer\nof the excited photocatalyst with alkenes, followed by the single\nelectron reduction, protonation, and subsequent single electron oxidation\nto afford the key alkyl carbocation intermediate. This protocol exhibits\nadvantages of broad functional group tolerance, excellent atom economy,\nhigh efficiency, and mild reaction conditions.

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Photoredox-Catalyzed\nMarkovnikov Hydroamination of\nAlkenes with Azoles · Figshare (2024) | TGRS Research Map | TGRS