Palladium-catalyzed synthesis of 2,3-disubstituted indoles via arylation of ortho-alkynylanilines with arylsiloxanes

In this study, we report the electrophilic cyclization of N,N-dimethyl-o-alkynylanilines with arylsiloxanes in the presence of [Pd(OAc)(2)] and Ag2O catalytic system, which leads to the efficient synthesis of indoles, similar to the one that is obtained through Larock indole synthesis. A range of ar...

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Published inOrganic & biomolecular chemistry Vol. 21; no. 37; pp. 7602 - 7610
Main Authors Hsia, Yang-Ting, Lu, Yu-Lin, Bai, Rekha, Badsara, Satpal Singh, Lee, Chin-Fa
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 27.09.2023
Royal Society of Chemistry
Subjects
Chemical synthesis
Chemistry
Chemistry, Organic
Functional groups
Indoles
Palladium
Physical Sciences
Science & Technology
Substrates
FUNCTIONALIZATION
CROSS-COUPLING REACTIONS
SILOXANE
SOLID-PHASE
O-ALKYNYLTRIFLUOROACETANILIDES
ALKYNES
DERIVATIVES
ARYL CHLORIDES
CYCLIZATION
UNSYMMETRICAL BIARYLS
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Summary:In this study, we report the electrophilic cyclization of N,N-dimethyl-o-alkynylanilines with arylsiloxanes in the presence of [Pd(OAc)(2)] and Ag2O catalytic system, which leads to the efficient synthesis of indoles, similar to the one that is obtained through Larock indole synthesis. A range of aryl(trimethoxy)silanes with EDGs and EWGs were successfully utilized for the synthesis of a diverse variety of substituted indoles via the cleavage of the C-Si bond. This protocol exhibits good functional group tolerance and wide substrate scope to provide 2,3-diaryl-N-methylindoles in 26-88% yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00961k