N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aldehydes with Arylsulfonyl Indoles

3-(1-Arylsulfonylalkyl)indoles as electrophiles in the N-heterocyclic carbene-catalyzed umpolung reaction of aldehydes were realized for the first time. This intermolecular Stetter-type reaction features the commercially available catalyst and mild reaction conditions, providing α-(3-indolyl) ketone...

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Bibliographic Details
Published inOrganic letters Vol. 11; no. 15; pp. 3182 - 3185
Main Authors Li, Yi, Shi, Fu-Qiang, He, Qing-Li, You, Shu-Li
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.08.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HIGHLY ENANTIOSELECTIVE SYNTHESIS
THIAZOLIUM
KETENES
NUCLEOPHILIC ACYLATION
BENZOIN REACTIONS
4+2 CYCLOADDITION
ALKYLATION
STETTER REACTION
ADDITIONS
FLUORIDE
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/ol9013238

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Summary:3-(1-Arylsulfonylalkyl)indoles as electrophiles in the N-heterocyclic carbene-catalyzed umpolung reaction of aldehydes were realized for the first time. This intermolecular Stetter-type reaction features the commercially available catalyst and mild reaction conditions, providing α-(3-indolyl) ketone derivatives in high yields for a wide range of substrates.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol9013238