PhotocatalyticStrecker-Type Reaction for the Synthesisof Primary α‑Aminonitriles

A practical photoinduced direct N–O cleavage of oxime ethers via a single electron transfer (SET) process was developed, enabling controlled generation of N–H imines via iminyl radical intermediates. By employing this strategy, an efficient Strecker-type reaction was established to construct a variety of primary α-aminonitriles using TMSCN as a cyanide source. This protocol showed exceptional tolerance to various functional groups, delivering the corresponding products in good yields. Mechanistic investigations indicate the involvement of iminyl radicals and a radical/polar crossover sequence.

Publication Details

Journal
Figshare
Published
2025-03-17
DOI
https://doi.org/10.1021/acs.orglett.5c00491.s001
Primary Topic
Genetic and Environmental Crop Studies
Type
article
Field-Weighted Citation Impact
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article

PhotocatalyticStrecker-Type Reaction for the Synthesisof Primary α‑Aminonitriles

Figshare
Genetic and Environmental Crop Studies
article

PhotocatalyticStrecker-Type Reaction for the Synthesisof Primary α‑Aminonitriles

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Abstract

A practical photoinduced direct N–O cleavage of oxime ethers via a single electron transfer (SET) process was developed, enabling controlled generation of N–H imines via iminyl radical intermediates. By employing this strategy, an efficient Strecker-type reaction was established to construct a variety of primary α-aminonitriles using TMSCN as a cyanide source. This protocol showed exceptional tolerance to various functional groups, delivering the corresponding products in good yields. Mechanistic investigations indicate the involvement of iminyl radicals and a radical/polar crossover sequence.

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Openalex Percentile: Top 41%
Genetic and Environmental Crop Studies
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PhotocatalyticStrecker-Type Reaction for the Synthesisof Primary α‑Aminonitriles · Figshare (2025) | TGRS Research Map | TGRS