Rhodium-Catalyzed Oxidative Annulation of 2- or 7-Arylindoles with Alkenes/Alkynes Using Molecular Oxygen as the Sole Oxidant Enabled by Quaternary Ammonium Salt

Developing an efficient catalytic system using molecular oxygen as the oxidant for rhodium-catalyzed cross-dehydrogenative coupling remains highly desirable. Herein, rhodium-catalyzed oxidative annulation of 2- or 7-phenyl-1H-indoles with alkenes or alkynes to assemble valuable 6H-isoindolo[2,1-a]in...

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Published inMolecules (Basel, Switzerland) Vol. 26; no. 17; p. 5329
Main Authors Zhuang, Weihui, Zhang, Jiaqi, Zheng, Yanping, Huang, Qiufeng
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 02.09.2021
MDPI
Subjects
2- or 7-arylindoles
Alkenes
Alkynes
Ammonium
Ammonium salts
Catalysis
Chemical reactions
Dehydrogenation
Experiments
Indoles
Michael reaction
molecular oxygen
Organic chemistry
Oxidants
oxidative annulation
Oxidizing agents
quaternary ammonium salt
Quaternary ammonium salts
Rhodium
rhodium catalysis
Spectrum analysis
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Summary:Developing an efficient catalytic system using molecular oxygen as the oxidant for rhodium-catalyzed cross-dehydrogenative coupling remains highly desirable. Herein, rhodium-catalyzed oxidative annulation of 2- or 7-phenyl-1H-indoles with alkenes or alkynes to assemble valuable 6H-isoindolo[2,1-a]indoles, pyrrolo[3,2,1-de]phenanthridines, or indolo[2,1-a]isoquinolines using the atmospheric pressure of air as the sole oxidant enabled by quaternary ammonium salt has been accomplished. Mechanistic studies provided evidence for the fast intramolecular aza-Michael reaction and aerobic reoxidation of Rh(I)/Rh(III), facilitated by the addition of quaternary ammonium salt.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26175329