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, furn...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 139; no. 36; pp. 12390 - 12393
Main Authors Dai, Jin-Ling, Shao, Nan-Qi, Zhang, Jin, Jia, Run-Ping, Wang, Dong-Hui
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.09.2017
Amer Chemical Soc
Subjects
Amines - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Copper - chemistry
Methylation
Phenols - chemistry
Physical Sciences
Science & Technology
ARYL BROMIDES
OXIDATION
EFFICIENT APPROACH
ARENES
COMPLEXES
PHOTOREDOX/NICKEL DUAL CATALYSIS
ORTHO-ARYLATION
SINGLE-ELECTRON TRANSMETALATION
H BOND FUNCTIONALIZATION
ARYLBORONIC ACIDS
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b06785