title: Pd(II)-mediated cyclization of o-allylbenzaldehydes in water: a novel synthesis of isocoumarins.
abstract: A novel, concise and efficient synthesis of substituted isocoumarins is disclosed. o-Allylbenzaldehydes prepared from isovanillin were mediated by PdCl(2)-CuCl(2) in water to undergo a domino reaction sequence, including 6-exo-trig cyclization, the addition of water, the elimination of PdHCl, the isomerization of carbon-carbon double bond, the oxidation of hemiacetals with the elimination of PdHCl, and regeneration of PdCl(2)in situ to yield a series of new substituted isocoumarins in high yields, in one pot.
authors.affiliation: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
authors.forename: Po-Yuan
authors.initials: PY
authors.lastname: Chen
authors.forename: Keng-Shiang
authors.initials: KS
authors.lastname: Huang
authors.forename: Chin-Chuan
authors.initials: CC
authors.lastname: Tsai
authors.forename: Tzu-Pin
authors.initials: TP
authors.lastname: Wang
authors.forename: Eng-Chi
authors.initials: EC
authors.lastname: Wang
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D049934:Isocoumarins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water
chemical_list: D001547:Benzaldehydes; D049934:Isocoumarins; D014867:Water; C093382:isovanillin; D010165:Palladium; D003300:Copper; C008756:palladium chloride; C029892:cupric chloride