Co-reporter:Wenhua Huang, Hong-Ying Rong, and Jie Xu
The Journal of Organic Chemistry 2015 Volume 80(Issue 13) pp:6628-6638
Publication Date(Web):June 12, 2015
DOI:10.1021/acs.joc.5b01031
Cyclic α-alkoxyphosphonium salts have been synthesized from (2-(diphenylphosphino)phenyl)methanol and aldehydes in 36–89% yields. These phosphonium salts are bench-stable solids and undergo Wittig olefination with aldehydes under basic conditions (K2CO3 or t-BuOK) to form benzylic vinyl ethers, which are readily hydrolyzed to 1,2-disubstituted ethanones under acidic conditions. The formation mechanism of these phosphonium salts via hemiacetal is also proposed.