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Published September 5, 2018 | Version Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon Wuhan University
  • 2. ROR icon California Institute of Technology

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.

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Supplemental Material - ja8b07597_si_001.pdf

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Additional details

Additional titles

Alternative title
General and Practical KOMe/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides

Identifiers

Eprint ID
88604
Resolver ID
CaltechAUTHORS:20180806-125449354

Funding

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

Dates

Created
2018-08-06
Created from EPrint's datestamp field
Updated
2021-11-16
Created from EPrint's last_modified field