Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 36, Pages 12390-12393Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b06785
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Funding
- National Key R&D Program of China [2016YFA0202900]
- Chinese Academy of Sciences [XDB20000000]
- Thousand Recruitment Program for Young Professionals
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A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford C-sp2-C-sp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical coupling mechanism involving a six-membered transition state is proposed to rationalize the high levels of ortho-selectivity in the reaction. This protocol provides straightforward access to ortho-aminomethyl-substituted phenols, unnatural amino acids and other bioactive small molecules.
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