4.8 Article

Photoredox-Mediated Generation of gem-Difunctionalized Ketones: Synthesis of α,α-Aminothioketones

Journal

ORGANIC LETTERS
Volume 21, Issue 12, Pages 4793-4797

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01677

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Funding

  1. CSIR [P-81-113]
  2. DBT, New Delhi [1151/2016]

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A photoredox-mediated gem-difunctionalization of alkynes leading to the synthesis of alpha,alpha-aminothio-substituted carbonyl compounds is reported. The work presents concomitant introduction of alpha-C-N and C-S bonds as a key enabling advance. Furthermore, the low bond dissociation energy of the C-S bond compared to that of C-N or C-C bonds has been exploited for selective functionalization using different nucleophiles to build diverse alpha,alpha-disubstituted carbonyl scaffolds. Mild reaction conditions, broad substrate scope, and good yields are some of the added advantages of this reaction.

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