Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates

A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael ad...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 12; pp. 4570 - 4574
Main Authors Yan, Tingting, Babu, Kaki Raveendra, Wu, Yong, Li, Yang, Tang, Yuhai, Xu, Silong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.06.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
PHOSPHORUS YLIDES
OLEFINS
ALLENES
ANNULATION
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Summary:A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01214