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. doi:10.1021/jacs.8b07597. https://resolver.caltech.edu/CaltechAUTHORS:20180806-125449354
![[img]](https://authors.library.caltech.edu/style/images/fileicons/application_pdf.png) |
PDF
- Accepted Version
See Usage Policy. 770kB |
|
PDF (Experimental procedures, characterization data and NMR spectra for all new compounds)
- Supplemental Material
See Usage Policy. 21MB |
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20180806-125449354
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: |
| ||||||||||||||||
| ORCID: |
| ||||||||||||||||
| 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: |
| ||||||||||||||||
| Issue or Number: | 35 | ||||||||||||||||
| DOI: | 10.1021/jacs.8b07597 | ||||||||||||||||
| Record Number: | CaltechAUTHORS:20180806-125449354 | ||||||||||||||||
| Persistent URL: | https://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: | 16 Nov 2021 00:28 |
Repository Staff Only: item control page
