Highly regioselective synthesis of 2,3-disubstituted indenes via a novel palladium-catalyzed cyclization reaction of propargylic carbonates with carbon nucleophiles.

Palladium-catalyzed reaction of propargylic carbonates with carbon nucleophiles offers an efficient, direct route to highly substituted indenes. The reaction conditions and the scope of the process are examined, and a possible mechanism is proposed. [reaction: see text]

[1]  Xinhua Duan,et al.  Synthesis of 2-substituted 3-aroylindenes via palladium-catalyzed carbonylative cyclization of diethyl 2-(2-(1-alkynyl)phenyl)malonates with aryl halides. , 2006, Organic letters.

[2]  Xinhua Duan,et al.  Synthesis of indenes via palladium-catalyzed carboannulation of diethyl 2-(2-(1-alkynyl)phenyl)malonate and organic halides. , 2006, The Journal of organic chemistry.

[3]  Xinhua Duan,et al.  Palladium-catalyzed one-pot synthesis of highly substituted furans by a three-component annulation reaction. , 2005, The Journal of organic chemistry.

[4]  M. Ihara,et al.  Facile syntheses of substituted 2,3-dihydrofurans and benzofurans by palladium-catalyzed reactions of propargylic carbonates with nucleophiles , 2004 .

[5]  M. Ihara,et al.  A novel methodology for the synthesis of cyclic carbonates based on the palladium-catalyzed cascade reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, involving a novel carbon dioxide elimination-fixation process. , 2003, Journal of the American Chemical Society.

[6]  M. Mori,et al.  Synthesis of different ring-size heterocycles from the same propargyl alcohol derivative by ligand effect on Pd(0) , 2002 .

[7]  D. Sinou,et al.  Palladium-catalyzed synthesis of 2,3-dihydro-2-ylidene-1,4-benzodioxins. , 2001, The Journal of organic chemistry.

[8]  M. Ihara,et al.  Palladium-Catalyzed Domino Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols: A Novel Synthetic Method for Cyclic Carbonates with Recycling of CO2. , 2001, Angewandte Chemie.

[9]  D. Sinou,et al.  An easy palladium-catalyzed access to 2-alkylidene-1,4-benzodioxanes , 1999 .

[10]  M. Ihara,et al.  Palladium-catalyzed cascade ring expansion reaction of 1-(3-methoxycarbonyloxy-1-propynyl)cyclobutanols with phenols , 1999 .

[11]  D. Sinou,et al.  Palladium(0) Cyclisation of 1-Aryl-6-hydroxy-2-hexynyl Carbonates: A New Way to Dihydropyrans , 1996 .

[12]  J. Tsuji,et al.  Palladium‐Catalyzed Reactions of Propargylic Compounds in Organic Synthesis , 1996 .

[13]  C. Frost,et al.  Selectivity in palladium catalysed allylic substitution , 1992 .

[14]  Xiyan Lu,et al.  Prop-2-ynylic carbonates as a1,a2 synthons in palladium catalysed annulation reactions with bifunctional nucleophiles , 1992 .

[15]  Geng Lifeng,et al.  Propargylic carbonates as an a1, a2 synthon in annulation reactions. A convenient synthesis of 3-methylene dihydropyran derivatives , 1990 .

[16]  I. Minami,et al.  A new furan annelation reaction by the palladium-catalyzed reaction of 2-alkynyl carbonates or 2-(1-alkynyl)oxiranes with β-keto esters , 1987 .

[17]  J. Tsuji.  New general synthetic methods involving π-allylpalladium complexes as intermediates and neutral reaction conditions , 1986 .

[18]  I. Minami,et al.  Novel palladium-catalyzed reactions of propargyl carbonates with carbonucleophiles under neutral conditions , 1985 .

[19]  Takashi Takahashi,et al.  Preparation of five- and six- membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis , 1980 .

[20]  J. Tsuji,et al.  Carbon-carbon bond formation via palladium complexes , 1969 .

[21]  J. Tsuji,et al.  Organic syntheses by means of noble metal compounds XVII. Reaction of π-allylpalladium chloride with nucleophiles☆ , 1965 .