Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 91, Issue 2, Pages 211-222Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20170316
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Funding
- Ministry of Education, Culture, Sports, Science and Technology
- JST Strategic Basic Research Programs Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) from Japan Science and Technology Agency [JPMJCR12YS]
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Rhodium-catalyzed alkylation reactions of C-H bonds (hydroarylation) in aromatic amides that contain an 8-amino-quinoline as a directing group with alkenes are discussed. Various alkenes, including acrylic esters, styrenes, alpha, beta-unsaturated butyrolactones, dihydrofurans, maleimides, and norbornene derivatives are applicable to this C-H alkylation. The reaction with norbornene gives unusual endo-hydroarylation products in a high degree of selectivity. The use of a carboxylic acid as an additive dramatically increases both the reactivity and the selectivity of the reaction. The results of deuterium-labeling experiments suggest that hydrometalation or carbo-metalation, which are commonly accepted mechanisms for C-H alkylation reactions, are not involved. Instead, the reaction appears to proceed through a rhodium carbene intermediate generated from the alkene.
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