4.8 Article

Photoinduced Phosphorylation/Cyclization of Cyanoaromatics for Divergent Access to Mono- and Diphosphorylated Polyheterocycles

Journal

ORGANIC LETTERS
Volume 23, Issue 24, Pages 9348-9352

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03360

Keywords

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Funding

  1. NSFC [21871257, 21801240, 21772163, 41876072]
  2. Natural Science Foundation of Fujian Province [2017J06007]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. NFFTBS [J1310024]

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The study describes a visible-light-driven switchable phosphorylation reaction for the synthesis of phosphorylated polyheterocycles, featuring high selectivity and functional group tolerance under mild reaction conditions. These findings may lead to the exploration of new photocatalytic applications of P(O)-H compounds by utilizing CN-containing substrates as radical acceptors.
The visible-light-driven switchable phosphorylation of cyanoaromatics with the 1,6-enyne moiety for the diverse and selective synthesis of phosphorylated polyheterocycles, including phosphorylated aminophosphonates, iminophosphonates, and ketones, has been described. Importantly, these photocatalytic transformations feature good functional group tolerance and high regio- and chemoselectivities under mild reaction conditions. These findings might stimulate the exploration of new photocatalytic utilizations of P(O)-H compounds by employing CN-containing substrates as the radical acceptors.

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