Visible-Light Photocatalytic Functionalization of Isocyanides for the Synthesis of Secondary Amides and Ketene Aminals | Zendy

Rolando Cannalire | Zendy; Jussara Amato | Zendy; Vincenzo Summa | Zendy; Ettore Novellino | Zendy; Gian Cesare Tron | Zendy; Mariateresa Giustiniano | Zendy

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Visible-Light Photocatalytic Functionalization of Isocyanides for the Synthesis of Secondary Amides and Ketene Aminals

Author(s) -

Rolando Cannalire,

Jussara Amato,

Vincenzo Summa,

Ettore Novellino,

Gian Cesare Tron,

Mariateresa Giustiniano

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c01946

Subject(s) - chemistry , ketene , ketenimine , photocatalysis , nucleophile , geminal , photochemistry , isocyanide , combinatorial chemistry , visible spectrum , organic chemistry , surface modification , wolff rearrangement , photoredox catalysis , catalysis , optoelectronics , physics

A new visible light-induced photocatalytic protocol enabling the formation of secondary amides from electron-poor organic bromides and isocyanides was developed. In addition, the in situ interception of ketenimine intermediates with nitrogen nucleophiles such as amines, hydrazines, and TMSN 3 afforded, in a one-pot two-step procedure, valuable scaffolds such as ketene aminals, pyrazolones, and tetrazoles. Mechanistic evidence confirmed a radical pathway where isocyanides acted as radical geminal acceptors generating key imidoyl radical species.

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