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Tuesday, August 25 • 4:00pm - 4:20pm
[0175] Synthesis and application of 2-substituted 1,1-diphenyl-2,4-dihydro-1H-benzo[d][1,3]oxaphosphinin-1-ium

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In the presence of Ph3PBr2 or Ph3PHBF4, 2-substituted 1,1-diphenyl-2,4-dihydro-1H-benzo[d][1,3]oxaphosphinin-1-ium can be synthesized from (2-(diphenylphosphino)phenyl)methanol and an aldehyde in 36-89% yields. These phosphonium salts are bench-stable solids and undergo Wittig olefination with another aldehyde under basic condition (K2CO3 or t-BuOK) to form benzylic vinyl ethers, which are readily hydrolyzed to 1,2-disubstitued ethanones under acidic condition. Therefore, the overall reaction provides a facile route to couple two aldehydes to form 1,2-disubstituted ethanones

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Tuesday August 25, 2015 4:00pm - 4:20pm PDT
Girvetz 2116