Copper-Catalyzed Regioselective Reaction of Internal Alkynes and Diaryliodonium Salts

The copper-catalyzed highly regioselective reaction of internal alkynes with diaryliodonium salts was achieved for the first time. α-Arylketones were obtained in moderate to good yields from arylpropargylic alcohols or aryl alkyl alkynes under mild conditions. It was found that the two kinds of subs...

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Published inOrganic letters Vol. 15; no. 9; pp. 2096 - 2099
Main Authors Xu, Ze-Feng, Cai, Chen-Xin, Liu, Jin-Tao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2013
Amer Chemical Soc
Subjects
Alkynes - chemistry
Biphenyl Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Molecular Structure
Onium Compounds - chemistry
Palladium - chemistry
Physical Sciences
Salts - chemistry
Science & Technology
Stereoisomerism
ROOM-TEMPERATURE
PALLADIUM
ONE-POT SYNTHESIS
ENANTIOSELECTIVE ALPHA-ARYLATION
CU-II
EFFICIENT
HYDRATION
WATER
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Summary:The copper-catalyzed highly regioselective reaction of internal alkynes with diaryliodonium salts was achieved for the first time. α-Arylketones were obtained in moderate to good yields from arylpropargylic alcohols or aryl alkyl alkynes under mild conditions. It was found that the two kinds of substrates underwent two different arylation–oxygenation pathways under different reaction conditions based on deuterated experiments, controlling experiments, and spectroscopic analysis of reaction intermediates.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4003543