Abstract

ORGANIC PREPARATIONS AND PROCEDURES INT, 27 (2), 127-160 (1995) PALLADIUM- AND/OR COPPER-MEDIATED CROSS-COUPLING REACTIONS BETWEEN 1-ALKYNES AND VINYL, ARYL, 1-ALKYNYL, lJ-PROPADIENYL, PROPARGYL AND ALLYLIC HALIDES OR RELATED COMPOUNDS. A REVIEW Reno Rossi*, Adriano Carpita and Fabio Bellina Dipartimento di Chimica e Chimica Industriale, Universita di Pisa Via Risorgimento 35,1-56126 Pisa, ITALY INTRODUCTION ............................................................................................................................ 129 I. Synthesis of Disubstituted Acetylenes via Palladium-copper Mediated Reaction of l-Alkynes with $-Carbon Halides ....................................................................................... 130 II. Synthesis of Heterocycles via Palladiumcopper Mediated Reaction of 1-Alkynes with (Heter0)aryl Halides ................................................................................................................. 138 III. Application of the Palladium-copper Mediated Reaction of 1-Alkynes with s$-Carbon Halides to the Synthesis of Natural Products and their Analogues .................................... 143 IV. Palladium Mediated Reactions between 1-Alkynes and Vinyl or Aryl Perfluomalkane sulfonates ................................................................................................................................... 144 V. Palladium Mediated Reactions between ldlkynes and Propargyl Derivatives, AUenyl Bromides or 1-Halo-1-alkynes ................................................................................................ 149 VI. Copper Mediated Reactions between 1-Alkynes and Aryl Iodides, Vinyl Iodides, AUyl Halides or Propargyl Derivatives ........................................................................................... 150 REFERENCES ................................................................................................................................. 152 Q 1995 by Organic F'reparations and Procedures Ine. 127 CROSS-COUPLINGREACIlONSBFIWEENl-ALKYNFSAND HALIDESCOMPOUNDS.AREVIEW PALLADIUM- AND/OR COPPER-MEDIATED CROSS-COUPLING REACTIONS BETWEEN 1-ALKYNES AND VINYL, ARYL, 1-ALKYNYL, 1J-PROPADIENYL, PROPARGYL AND ALLYLIC HALIDES OR RELA'ED COMPOUNDS. A REVIEW Renzo Rossi*, Adriano Carpita and Fabio Bellina Dipartimento di