Palladium(II)-Catalyzed Mono- and Bis-alkenylation of N‑Acetyl-2-aminobiaryls through Regioselective C–H Bond Activation

We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C–H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono- and bis-alkenylation products with the solvent effect. The developed p...

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Published inJournal of organic chemistry Vol. 83; no. 7; pp. 3840 - 3856
Main Authors Annamalai, Pratheepkumar, Hsu, Kou-Chi, Raju, Selvam, Hsiao, Huan-Chang, Chou, Chih-Wei, Lin, Gu-Ying, Hsieh, Cheng-Ming, Chen, Pei-Ling, Liu, Yi-Hung, Chuang, Shih-Ching
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.04.2018
Amer Chemical Soc
Subjects
alkenes
carbon-hydrogen bond activation
catalytic activity
chemical bonding
chemical reactions
Chemistry
Chemistry, Organic
moieties
organic chemistry
palladium
Physical Sciences
protocols
regioselectivity
Science & Technology
solvents
O-ARYLANILINES
OLEFINATION
ONE-POT SYNTHESIS
ANNULATION
ALKYLATION
ARYLATION
ARYL IODIDES
DIRECTING-GROUP
ALKYNES
INDOLES
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.8b00194

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Summary:We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C–H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono- and bis-alkenylation products with the solvent effect. The developed protocol was promising for a broad substrate scope ranging from activated olefins with a wide variety of functional groups to unactivated olefins.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b00194