Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols

Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols
Dong-Hui Wang, Run-Ping Jia, Jin Zhang, Jin-Ling Dai, Nan-Qi Shao
A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2–Csp3 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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06785

DOI: 10.1021/jacs.7b06785

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