4.7 Article

Synthesis of Functionalized Spirocyclic Indolines by Visible Light-Induced One-Pot Sequential Difluoromethylative Dearomatization, Hydroxylation, and Substitution Reactions

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 20, Pages 4739-4747

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900755

Keywords

one-pot reaction; 3,3 '-spirocyclic indoline; phosphination; indolization; fungicidal activity

Funding

  1. National Key Research and Development Program of China [2018YFD0200100]
  2. National Natural Science Foundation of China [21732002, 21672117, 21772102]

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Herein we describe an one-pot protocol for visible light-induced synthesis of functionalized spirocyclic indolines under mild conditions by means of a process involving sequential difluoromethylative dearomatization, hydroxylation, and substitution reactions of indole derivatives. The transformation proceeds via a hydroxylated acetal pool intermediate that can react with various nucleophiles. Several of the phosphine-oxide and indole-substituted products showed good fungicidal activity, suggesting that this protocol might be useful in the agrochemical field.

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