Facile and selective deallylation of allyl ethers using diphosphinidenecyclobutene-coordinated palladium catalysts.
(pi-Allyl)palladium triflate bearing a 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-tert-butylphenylphosphinidene)cyclobutene ligand (DPCB-OMe), [Pd(eta(3)-C(3)H(5))(DPCB-OMe)]OTf, efficiently catalyzes deallylation of a variety of allyl ethers in aniline to give corresponding alcohols in high yields under mild conditions. The reactions can be performed in air without loss of a variety of functionalities including vinyl, alkynyl, hydroxy, acetoxy, silyloxy, and acetal groups. Allyl 2-allyloxybenzoate selectively undergoes deallylation of the allyloxy group to give allyl salicylate in quantitative yield.
Murakami
Hiromi
H
Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Minami
Tatsuya
T
Ozawa
Fumiyuki
F