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 in | Organic letters Vol. 17; no. 13; pp. 3283 - 3285 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
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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. |
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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 – name: Chinese Academy of Sciences – name: Instrumental Analysis and Research Center of Shanghai University – name: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry – name: Department of Chemistry, Innovative Drug Research Center – name: Laboratory for Microstructures |
Author_xml | – sequence: 1 givenname: Dandan surname: Shen fullname: Shen, Dandan – sequence: 2 givenname: Jing surname: Han fullname: Han, Jing – sequence: 3 givenname: Jie surname: Chen fullname: Chen, Jie – sequence: 4 givenname: Hongmei surname: Deng fullname: Deng, Hongmei – sequence: 5 givenname: Min surname: Shao fullname: Shao, Min – sequence: 6 givenname: Hui surname: Zhang fullname: Zhang, Hui email: yehao7171@shu.edu.cn – sequence: 7 givenname: Weiguo surname: Cao fullname: Cao, Weiguo email: wgcao@staff.shu.edu.cn |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26090551$$D View this record in MEDLINE/PubMed |
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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 |
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