Suzuki coupling of 2-chloroacrylonitrile, methyl 2-chloroacrylate, or 2-chloroprop-1-en-3-ol with arylboronic acids catalyzed by a palladium-tetraphosphine complex

The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane (Tedicyp) in combination with [Pd(C3H5)Cl](2) affords an efficient catalyst of the coupling of 2-chloroacrylonitrile with arylboronic acids. In the presence of 1% catalyst, the 2-arylacrylonitrile derivatives were obtained in medium to good yields. A variety of substituents such as alkyl, methoxy, fluoro, trifluoromethyl, formyl, or nitro on the arylboronic acid are tolerated. The cross-coupling reactions of methyl 2-chloroacrylate with arylboronic acids give simple access to 2-phenylacrylate derivatives, which are useful precursors for the synthesis of biologically active compounds such as ibuprofen, ketoprofen, and naproxen.