4.7 Article

Visible-Light-Promoted Regio- and Stereoselective Oxyalkenyl-Ation of Phosphinyl Allenes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 13, Pages 2701-2708

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000214

Keywords

Phosphinyl Allenes; Oxyalkenylation; Visible Light; Palladium Catalysis; Conjugated Tertiary Allylic Alcohol derivatives

Funding

  1. Foundation Research Project of Jiangsu Province (The Natural Science Foundation) [BK20180513, BK20191305]
  2. Fundamental Research Funds for the Central Universities (NJAU) [KYDZ201904, KJQN201719]
  3. Qing-Lan Project of Jiangsu Provincial Department of Education
  4. 333 High Level Talent Project of Jiangsu Province

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A highly regio- and stereoselective oxyalkenylation of phosphinyl allenes is revealed for the first time. This protocol, merging visible light photoredox and palladium catalysis, provides a direct approach to conjugated tertiary allylic alcohol derivatives with broad functional group tolerance in moderate to excellent yields. Mechanistic studies suggest that, although two possible pathways exist in the transformation, radical oxyalkenylation promoted by visible light photoredox takes over the major pathway.

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