Cyclodehydration of cis–2-butene-1,4-diol with active methylene compounds catalyzed by a diphosphinidenecyclobutene-coordinated palladium complex

(π-Allyl)palladium triflate coordinated with 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-t-butylphenylphosphinidene)cyclobutene (DPCB–OMe), [Pd(η3-C3H5)(DPCB–OMe)]OTf, efficiently catalyzes cyclodehydration of cis–2-butene-1,4-diol with active methylene compounds such as acetylacetone and ethyl acetoacetate in toluene in the presence of pyridine. The reactions can be performed in air, giving 2-vinyl-2,3-dihydrofurans in good to high yields.

Complex 1 coordinated with 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-t-butylphenylphosphinidene)cyclobutene (DPCB–OMe) efficiently catalyzes cyclodehydration of cis–2-butene-1,4-diol with active methylene compounds to give 2-vinyl-2,3-dihydrofurans in good to high yields.Figure optionsDownload as PowerPoint slide