Regioselective Control in the Palladium-Catalyzed Isomerization of Methylenecyclopropylcarbinols Using Acetic Acid as a Reagent

Min Shi; Bao-Yu Wang; Li-Xiong Shao

doi:10.1055/s-2007-973871

LETTER

Regioselective Control in the Palladium-Catalyzed Isomerization of Methylenecyclopropylcarbinols Using Acetic Acid as a Reagent

Min Shi*, Bao-Yu Wang, Li-Xiong Shao
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: Mshi@mail.sioc.ac.cn;

Abstract

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Abstract

Tuning the regioselectivity of the Pd-catalyzed isomerization of methylenecyclopropylcarbinols in acetic acid is achieved by a subtle choice of the ligand and/or solvent. When dioxane is used as the solvent, penta-2,4-dien-1-ols are formed, whereas when AsPh₃ is used as the ligand and toluene is used as the solvent, pent-4-enals are formed. A plausible reaction mechanism is discussed on the basis of the control experiments.

Key words

regioselectivity - palladium-catalyzed isomerization - methylenecyclopropylcarbinols - acetic acid

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Referenzen

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