Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 8, Pages 3184-3191Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo060104d
Keywords
-
Categories
Ask authors/readers for more resources
The Pd(II)-catalyzed reaction of arylboronic acids and internal alkynes provides a convenient route to a wide variety of tetrasubstituted olefins. The reaction is conducted in DMSO using molecular O-2 as an oxidant in the absence of any base. The reaction involves the cis addition of two aryl groups from the arylboronic acid to opposite ends of the triple bond of the internal alkyne. The synthesis tolerates a wide variety of functional groups, including alcohol, aidehyde, ester, TMS, and acetal groups. Electron-rich dialkylacetylenes, such as 4-octyne, provide highly substituted 1,3-dienes in moderate yields. The very mild O-2/DMSO conditions also afford good to excellent yields of biaryls by the homocoupling of arylboronic acids.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available