Efficient double bond migration of allylbenzenes catalyzed by Pd(OAc)_2-HFIP system with unique substituent effect

Nishiwaki, Nagatoshi, Kamimura, Ryuichiro, Shono, Kimihiro, Kawakami, Toshihiko, Nakayama, Katsuhisa, Nishino, Kohei, Nakayama, Takayuki, Takahashi, Keisuke, Nakamura, Aki, Hosokawa, Takahiro

doi:10.1002/chin.201040057

Efficient double bond migration of allylbenzenes catalyzed by Pd(OAc)_2-HFIP system with unique substituent effect

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書誌事項

タイトル別名

ChemInform Abstract: Efficient Double Bond Migration of Allylbenzenes Catalyzed by Pd(OAc)<sub>2</sub>—HFIP System with Unique Substituent Effect.

公開日: 2010

資源種別: journal article

DOI

10.1016/j.tetlet.2010.05.014
10.1002/chin.201040057

公開者: Elsevier Ltd.

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説明

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 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 chloro substituents.