Journal
ACS CATALYSIS
Volume 10, Issue 18, Pages 10516-10522Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c02522
Keywords
palladium; alkenes; C-H activation; silylation; borylation
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Funding
- NSF of China [21672075, 21822303, 21772020]
- Instrumental Analysis Center of Huaqiao University
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A palladium/DPEphos-catalyzed intermolecular trans-selective carbofunctionalization of internal alkynes has been established herein. This method proceeds through a formal anti-carbopalladation, forming trans-alkenyl palladium species, which was trapped by aryl boronic acids to provide all-carbon tetrasubstituted alkenes in 32-92% yields. The trans-selective arylsilylation/remote C-H silylation and hydroarylation/remote C-H borylation of internal alkynes were also achieved using hexamethyldisilane and bis(pinacolato)diboron as trapping reagents, respectively. The reaction features good regio- and stereoselectivity and high functional group tolerance. A preliminary mechanistic study and DFT calculations show that a cis to trans isomerization of cis-alkenyl palladium species was involved in this transformation.
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