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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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
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Abstract 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.
AbstractList 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.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.
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.
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 degrees 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.
Author Zhang, Hui
Shen, Dandan
Deng, Hongmei
Shao, Min
Cao, Weiguo
Han, Jing
Chen, Jie
AuthorAffiliation Chinese Academy of Sciences
Shanghai University
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry
Department of Chemistry, Innovative Drug Research Center
Laboratory for Microstructures
Instrumental Analysis and Research Center of Shanghai University
AuthorAffiliation_xml – name: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry
– name: Shanghai University
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– name: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry
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Issue 13
Keywords FUNCTIONALIZATION
FACILE SYNTHESIS
ANNULATION
ANILINES
INDOLE SYNTHESIS
BOND
REGIOSELECTIVITY
C-H ACTIVATION
DERIVATIVES
CYCLIZATION
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Snippet 2-Perfluoroalkylated indoles were efficiently synthesized via a one-pot cascade Michael-type addition/palladium-catalyzed intramolecular cross-dehydrogenative...
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SubjectTerms chemical reactions
Chemistry
Chemistry, Organic
dimethyl sulfoxide
indoles
moieties
oxidants
oxygen
Physical Sciences
Science & Technology
synthesis
Title 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
URI http://dx.doi.org/10.1021/acs.orglett.5b01479
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https://www.ncbi.nlm.nih.gov/pubmed/26090551
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https://www.proquest.com/docview/2020864122
Volume 17
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