A One??Pot Sequence of Stille and Heck Couplings: Synthesis of Various 1, 3, 5??Hexatrienes and Their Subsequent 6π??Electrocyclizations

P von Zezschwitz, F Petry…

Index: Von Zezschwitz, Paultheo; Petry, Frauke; De Meijere, Armin Chemistry - A European Journal, 2001 , vol. 7, # 18 p. 4035 - 4046

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Citation Number: 55

Abstract

Abstract Palladium-catalyzed cross-coupling reactions of 2-bromocyclohex-1-enyl triflates 7 and 11 with a variety of alkenylstannanes occurred chemoselectively at the site of the triflate leaving group to give bromobutadienes which readily underwent Heck reactions with acrylates and styrene. Both steps could be performed in the same flask to give differentially functionalized hexatrienes in up to 88% overall yield. With simple stannanes, the same ...