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DOI: 10.1055/s-2007-991455
Chromatography-Free Allylic Cleavage
H. Tsukamoto*, T. Suzuki, M. Sato, Y. Kondo
Tohoku University, Sendai, Japan
Publikationsverlauf
Publikationsdatum:
18. Dezember 2007 (online)

Significance
A chromatography-free workup protocol for cleavage of allylalkyl ethers yielding the parent alkyl alcohols was developed. The palladium-catalyzed allylic Suzuki coupling of the allylalkyl ether was carried out with vinylboronic anhydride-pyridine complex in the presence of a catalytic amount of Pd(OAc)2 and 4-(diphenylphosphino)benzoic acid to give the desired parent alcohol and the volatile co-products. The crude reaction mixture was treated with polystyrene-bound diethanolamine (PS-DEAM) where the boronic ester underwent alcoholysis and the resulting boronic acid was scavenged by PS-DEAM. At the same workup step, the acidic phosphine (and/or phoshine oxide) and the palladium residue were trapped by PS-DEAM. The mixture was filtered and the filtrate was concentrated in vacuo to give the desired parent alcohol.