4.7 Article

Identification of Bond-Weakening Spirosilane Catalyst for Photoredox α-C-H Alkylation of Alcohols

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 2, Pages 337-343

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901253

Keywords

alcohols; bond-weakening; C-H activation; photoredox catalysis; regioselectivity; silicates

Funding

  1. JSPS [JP19J23157]
  2. JSPS KAKENHI [JP16H04239, JP18K06545, JP17H06442]

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The development of catalyst-controlled site-selective C(sp(3))-H functionalization is a current major challenge in organic synthesis. This paper describes DFT-guided identification of pentavalent silicate species as a novel bond-weakening catalyst for the alpha-C-H bonds of alcohols together with a photoredox catalyst and a hydrogen atom transfer catalyst. Specifically, Martin's spirosilane accelerated alpha-C-H alkylation of alcohols.

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