Gold-catalyzed highly chemo- and regioselective C-H bond functionalization of phenols with haloalkynes
A highly chemo- and stereoselective addition of unprotected phenols to haloalkynes was developed. A ligand and counterion controlled process enabled the highly site-selective and chemoselective C-H bond functionalization of phenol derivatives with haloalkynes in moderate to excellent yield at room t...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
06 May 2019
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| In: |
European journal of organic chemistry
Year: 2019, Issue: 24, Pages: 3867-3876 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201900653 |
| Online Access: | Resolving-System, Volltext: https://doi.org/10.1002/ejoc.201900653 Verlag: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201900653 
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| Author Notes: | Tapas Adak, Jürgen Schulmeister, Martin C. Dietl, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| Summary: | A highly chemo- and stereoselective addition of unprotected phenols to haloalkynes was developed. A ligand and counterion controlled process enabled the highly site-selective and chemoselective C-H bond functionalization of phenol derivatives with haloalkynes in moderate to excellent yield at room temperature. The simple availability of the starting materials in combination with the preferred para-C-H functionalization over a competing O-H insertion makes this an attractive protocol. The stereoselectivity of the products depends on the choice of the catalyst. From a synthetic prospective, this method offers an efficient route towards vinyl chlorides, which are valuable precursors for the synthesis of pharmaceutical drugs. |
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| Item Description: | Gesehen am 13.11.2019 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201900653 |