Visible‐Light‐Promoted Regio‐ and Stereoselective Oxyalkenyl‐ation of Phosphinyl Allenes

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 mo...

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Published inAdvanced synthesis & catalysis Vol. 362; no. 13; pp. 2701 - 2708
Main Authors Sun, Xue, Liu, Teng, Yang, Yan‐Tong, Gu, Yue‐Jie, Liu, Yu‐Wei, Ji, Yi‐Gang, Luo, Kai, Zhu, Jie, Wu, Lei
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 16.07.2020
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Conjugated Tertiary Allylic Alcohol derivatives
Functional groups
Oxyalkenylation
Palladium
Palladium Catalysis
Phosphinyl Allenes
Physical Sciences
Science & Technology
Stereoselectivity
Visible Light
CATALYSIS
MECHANISM
Oxyalkenylation
Palladium Catalysis
Conjugated Tertiary Allylic Alcohol derivatives
Phosphinyl Allenes
OXYGEN
FUNCTIONALIZATION
Visible Light
SYNTHETIC APPLICATIONS
AEROBIC OXIDATION
PHTHALOCYANINES
CYCLIZATION
TRIFLUOROMETHYLATION
PHOTOOXIDATION
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Summary: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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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000214