Efficient double bond migration of allylbenzenes catalyzed by Pd (OAc) 2–HFIP system with unique substituent effect

…, T Kawakami, K Nakayama, K Nishino, T Nakayama…

Index: Nishiwaki, Nagatoshi; Kamimura, Ryuichiro; Shono, Kimihiro; Kawakami, Toshihiko; Nakayama, Katsuhisa; Nishino, Kohei; Nakayama, Takayuki; Takahashi, Keisuke; Nakamura, Aki; Hosokawa, Takahiro Tetrahedron Letters, 2010 , vol. 51, # 27 p. 3590 - 3592

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Citation Number: 21

Abstract

A novel catalyst system of Pd (OAc) 2–HFIP induces double-bond migration of allylbenzenes under mild conditions with low catalytic loading to afford 1-propenylbenzenes. The reaction shows a unique substituent effect that is highly dependent on the distance of substituents from the allylic moiety. Thus, the reactivity of substrates bearing a methyl group is ordered in para> meta> ortho, whereas it is entirely reversed as ortho> meta> para for methoxy and ...