Palladium-catalyzed cross-coupling reaction of bis (pinacolato) diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1, 3-dienes via the …

…, K Takahashi, T Ishiyama, N Miyaura

Index: Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura, Norio Journal of the American Chemical Society, 2002 , vol. 124, # 27 p. 8001 - 8006

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Citation Number: 185

Abstract

The synthesis of 1-alkenylboronic acid pinacol esters via a palladium-catalyzed cross- coupling reaction of bis (pinacolato) diboron (pin2B2, pin= Me4C2O2) with 1-alkenyl halides or triflates was carried out in toluene at 50° C in the presence of KOPh (1.5 equiv) and PdCl2 (PPh3) 2-2Ph3P (3 mol%). The borylation of acyclic and cyclic 1-alkenyl bromides and triflates was achieved in high yields with complete retention of configuration of the double ...