Mild and Efficient One-Pot Synthesis of 2‑(Perfluoro­alkyl)­indoles by Means of Sequential Michael-Type Addition and Pd(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) Reaction

2-Perfluoroalkylated indoles were efficiently synthesized via a one-pot cascade Michael-type addition/palladium-catalyzed intramolecular cross-dehydrogenative coupling (CDC) process, using molecular oxygen as the sole oxidant at 100 °C in DMSO. This process allows atom economical assembly of indole...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 13; pp. 3283 - 3285
Main Authors Shen, Dandan, Han, Jing, Chen, Jie, Deng, Hongmei, Shao, Min, Zhang, Hui, Cao, Weiguo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.07.2015
Amer Chemical Soc
Subjects
chemical reactions
Chemistry
Chemistry, Organic
dimethyl sulfoxide
indoles
moieties
oxidants
oxygen
Physical Sciences
Science & Technology
synthesis
FUNCTIONALIZATION
FACILE SYNTHESIS
ANNULATION
ANILINES
INDOLE SYNTHESIS
BOND
REGIOSELECTIVITY
C-H ACTIVATION
DERIVATIVES
CYCLIZATION
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Summary:2-Perfluoroalkylated indoles were efficiently synthesized via a one-pot cascade Michael-type addition/palladium-catalyzed intramolecular cross-dehydrogenative coupling (CDC) process, using molecular oxygen as the sole oxidant at 100 °C in DMSO. This process allows atom economical assembly of indole rings from inexpensive and readily available anilines and methyl perfluoroalk-2-ynoates and tolerates a broad range of functional groups.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5b01479