Journal
ORGANIC LETTERS
Volume 10, Issue 19, Pages 4351-4353Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801763j
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Funding
- National Science and Engineering Research Council of Canada
- Merck Frosst Canada Co.
- University of Toronto
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A highly effective and operationally simple method for the regioselective deuteration of anilines is presented. A variety of electron-rich and electron-deficient anilines are efficiently deuterated at the ortho and/or para position with respect to the nitrogen in the presence of 1 equiv of conc HCl in D(2)O. Under the present conditions, aromatic methoxy groups do not facilitate deuteration, enabling a chemo- and regioselective deuteration of p-anisidine.
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