Introducing N -Sulfinylamines into Visible-Light-Induced Carbene Chemistry for the Synthesis of Diverse Amides and α-Iminoesters

A rare example of visible-light-mediated diverse reactivity of N-sulfinylamines with different types of carbene precursors has been disclosed. Acylsilanes and aryldiazoacetates have been utilized as nucleophilic and electrophilic carbene precursors into the N═S═O linchpin, to achieve valuable amides...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (47), p.8511-8515
Main Authors: Roy, Sourav, Biswas, Apurba, Paul, Hrishikesh, Ariyan, SK, Chatterjee, Indranil
Format: Article
Language:English
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Summary:A rare example of visible-light-mediated diverse reactivity of N-sulfinylamines with different types of carbene precursors has been disclosed. Acylsilanes and aryldiazoacetates have been utilized as nucleophilic and electrophilic carbene precursors into the N═S═O linchpin, to achieve valuable amides and α-iminoesters, respectively. Interestingly, diazocarbonyls can also participate in the amidation reaction with N-sulfinylamines via in situ generated ketenes. This operationally simple modular method offers a mild, transition-metal-free, and coupling-reagent-free protocol to fabricate structurally diverse amides and a promptly accessible technique to achieve α-iminoesters, where visible light remains as a key promoter.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03486