期刊
TETRAHEDRON LETTERS
卷 56, 期 45, 页码 6231-6235出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.09.100
关键词
H-D exchange; Palladium; NHC; CF3COOD
资金
- Hydrocarbon Research Foundation
- National Institute of Health [S10 RR025432]
A method has been developed for one-step ortho-selective ligand-directed H-D exchange, accompanied in some cases by concurrent acid-catalyzed electrophilic deuteration. This method is effective for deuteration of aromatic substrates ranging from ketones to amides and amino acids, including compounds of biological and pharmaceutical interest such as acetaminophen and edaravone. Use of a palladium catalyst featuring an NHC ligand is critical for the observed reactivity. Experimental evidence strongly suggests that palladium facilitates C-H activation of the aromatic substrates, a mechanism seldom observed under strongly acidic conditions. (C) 2015 Elsevier Ltd. All rights reserved.
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