Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols
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.
Preparation and NMR characterization of hydrogen bonding in 2- and 2,6-bis-(N,N-diethylaminomethyl)-4R-phenols
A series of Mannich mono- and di-bases derived from 4-substituted phenols were prepared and investigated by 1H and 13C NMR spectroscopy in chloroform-d1 solution.The chemical shifts of intramolecular hydrogen-bonded protons in Mannich bases depend on the
Brycki, Bogumil,Maciejewska, Hanna,Brzezinski, Bogumil,Zundel, Georg
p. 61 - 71
(2007/10/02)
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