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General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides

Xin Wang, Ming-Hui Zhu, David P Schuman, Dayou Zhong, Wen-Yan Wang, Lin-Yang Wu, Wei Liu, Brian M Stoltz, Wen-Bo Liu

J Am Chem Soc. 2018 Sep 5;140(35):10970-10974.

PMID: 30075628

Abstract:

Herein we describe a general, mild and scalable method for deuterium incorporation by potassium methoxide/hexamethyldisilane-mediated dehalogenation of arylhalides. With CD3CN as a deuterium source, a wide array of heteroarenes prevalent in pharmaceuticals and bearing diverse functional groups are labeled with excellent deuterium incorporation (>60 examples). The ipso-selectivity of this method provides precise access to libraries of deuterated indoles and quinolines. The synthetic utility of our method has been demonstrated by the incorporation of deuterium into complex natural and drug-like compounds.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP1590870 Disilane Disilane 1590-87-0 Price
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