Journal
CHEMICAL SCIENCE
Volume 10, Issue 38, Pages 8744-8751Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc03691a
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Funding
- National Natural Science Foundation of China [21772235]
- CAMS Innovation Fund for Medical Sciences [2017-I2M-3-011]
- Drug Innovation Major Project [2018ZX09711-001-005]
- Non-profit Central Research Institute Fund of the Chinese Academy of Medical Sciences [2018PT35003, 2019-RC-HL-008]
- China Postdoctoral Science Foundation [2017M620496]
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The limitations of arene C-H functionalization of aryl sulfonamides containing strongly coordinating Nheterocycles were overcome using a Rh(III) catalyst. The site-selectivity of C-H carbenoid functionalization at the ortho position relative to either the sulfonamide or N-heterocycle directing groups was elegantly switched using solvents of different polarities and different additive concentrations. Importantly, sulfonamide-group-directed ortho-C-H carbenoid functionalization tolerated strongly coordinating N-heterocycles, including pyridine, pyrrole, thiazole, pyrimidine, and pyrazine. Density functional theory (DFT) calculations were performed to rationalize the reaction mechanisms and the influence of reaction polarity.
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