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An Unexpected Reaction of Allylic Propynoate under Palladium(II) Catalysis
Author(s) -
Zhang ZhaoGuo,
Lu XiYan,
Lang ShenHui
Publication year - 2002
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20020201123
Subject(s) - chemistry , allylic rearrangement , palladium , catalysis , halide , medicinal chemistry , acrolein , reagent , substrate (aquarium) , heteroatom , ring (chemistry) , polymer chemistry , organic chemistry , oceanography , geology
Palladium (II) catalyzed reactions of allyl propynoate in the presence of excess halide ions with or without allyl halide or acrolein were studied, yielding ( E )‐3‐halo‐2‐allyl‐acrylic acid as the sole product. A mechanism involving halopalladation, carbopalladation, ring opening and β‐heteroatom elimination was proposed and was further justified by the reaction with deuterated substrate.