Patel, Monika ; Saunthwal, Rakesh K. ; Dhaked, Devendra K. ; Bharatam, Prasad V. ; Verma, Akhilesh K. (2015) Nucleophilic Addition versus SNAr Study: Chemo-, Regio- and Stereoselective Hydrothiolation of Haloaryl Alkynes over S-Arylation of Aryl Halides Asian Journal of Organic Chemistry, 4 (9). pp. 894-898. ISSN 2193-5807
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Official URL: http://doi.org/10.1002/ajoc.201500239
Related URL: http://dx.doi.org/10.1002/ajoc.201500239
Abstract
Base‐mediated regio‐, stereo‐, and chemoselective nucleophilic addition of thiophenols onto bromo‐substituted aryl alkynes over S‐arylation of aryl halides is described. The regio‐ and stereochemistry of the products is well supported by spectral studies and X‐ray crystallography. Competitive experiments showed that hydroamination is preferred over hydrothiolation. The stereoselectivity, competitive nucleophilic addition, and mechanistic pathway were corroborated by experimental and computational evidence.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley & Sons, Inc. |
| Keywords: | Alkynes; Aryl Halides; Hydrothiolation; S-arylation; Thiophenols. |
| ID Code: | 116400 |
| Deposited On: | 12 Apr 2021 09:31 |
| Last Modified: | 12 Apr 2021 09:31 |
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