Synlett

Functionalization of 2-alkylidenetetrahydrofurans and 2-alkylidenepyrrolidines by palladium (0)-catalyzed cross-coupling reactions

E Bellur, P Langer

Index: Bellur, Esen; Langer, Peter Synlett, 2004 , # 12 p. 2169 - 2171

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Citation Number: 12

Abstract

Palladium-catalyzed cross coupling reactions of 3a,b were studied (Scheme [1] , Table [1] ). Stille reactions of 3a with Me 3 SnPh or Bu 3 SnPh proved unsuccessful under a variety of conditions. In contrast, the Suzuki reaction of 3a with PhB(OH) 2 in the presence of Pd(PPh 3 ) 4 (3 mol%) afforded the desired 2-alkylidenetetrahydrofuran 4a. The best yields (up to 87%) were obtained when Pd(PPh 3 ) 4 , phenylboronic acid, K 3 PO 4 and dioxane ...