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

Wang, Xin and Zhu, Ming-Hui and Schuman, David P. and Zhong, Dayou and Wang, Wen-Yan and Wu, Lin-Yang and Liu, Wei and Stoltz, Brian M. and Liu, Wen-Bo (2018) General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides. Journal of the American Chemical Society, 140 (35). pp. 10970-10974. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20180806-125449354

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/jacs.8b07597DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jacs.8b07597PublisherSupporting Information
ORCID:
AuthorORCID
Liu, Wei0000-0001-6249-3179
Stoltz, Brian M.0000-0001-9837-1528
Liu, Wen-Bo0000-0003-2687-557X
Alternate Title:General and Practical KOMe/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides
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.
Funders:
Funding AgencyGrant Number
National Natural Science Foundation of China21602160
National Natural Science Foundation of China21772148
Fundamental Research Funds for the Central Universities2042018kf0017
NSFCHE-1700982
National Program for 1000 Young Talents of ChinaUNSPECIFIED
Wuhan UniversityUNSPECIFIED
CaltechUNSPECIFIED
Record Number:CaltechAUTHORS:20180806-125449354
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20180806-125449354
Official Citation: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, and Wen-Bo Liu. Journal of the American Chemical Society 2018 140 (35), 10970-10974. DOI: 10.1021/jacs.8b07597.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88604
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:06 Aug 2018 22:10
Last Modified:22 Mar 2019 17:06

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