Published September 5, 2018
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Journal Article
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General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides
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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.
Additional Information
© 2018 American Chemical Society. Received: July 18, 2018; Published: August 3, 2018. We gratefully acknowledge the NSFC (21602160, 21772148), the Fundamental Research Funds for the Central Universities (2042018kf0017), the NSF under the CCI Center for Selective C–H Functionalization (CCHF), CHE-1700982, National Program for 1000 Young Talents of China, Wuhan University, and Caltech for financial support. Prof. Qiang-Hui Zhou and his group are appreciated for generously sharing their lab space. Profs. Martin Oestreich (T.U. Berlin), Nasri Nesnas (F.I.T.), and Yong Liang (Nanjing Univ.) are thanked for helpful discussions. We also thank Dr. Hongbing Liu (Wuhan Institute of Physics and Mathematics, CAS) for the measurements of ^2H NMR spectra. The authors declare no competing financial interest. A provisional patent has been filed.Attached Files
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Additional details
- Alternative title
- General and Practical KOMe/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides
- Eprint ID
- 88604
- Resolver ID
- CaltechAUTHORS:20180806-125449354
- National Natural Science Foundation of China
- 21602160
- National Natural Science Foundation of China
- 21772148
- Fundamental Research Funds for the Central Universities
- 2042018kf0017
- NSF
- CHE-1700982
- National Program for 1000 Young Talents of China
- Wuhan University
- Caltech
- Created
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2018-08-06Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field