Smiles-Rearrangement-Based One-Pot Synthesis of Diarylacetylenes from Benzylic Sulfones and Methyl Benzoates Mediated by LiN(SiMe<sub>3</sub>)<sub>2</sub>/KN(SiMe<sub>3</sub>)<sub>2</sub>
The one-pot synthesis of diphenylacetylene by the reaction of methyl benzoate with 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene was developed. The combination of LiN(SiMe<sub>3</sub>)<sub>2</sub> and KN(SiMe<sub>3</sub>)<sub>2</sub> is key to promoting the reaction. Simply combining methyl benzoate, 1-(benzylsulfonyl)-3,5-di(trifluoromethyl)benzene, LiN(SiMe<sub>3</sub>)<sub>2</sub>, and KN(SiMe<sub>3</sub>)<sub>2</sub> can produce a variety of diaryl acetylenes (28 examples, 18-70% yields).
Authors
- Ruyuan Ma (ORCID: https://orcid.org/0009-0004-0737-1098)
- Yan‐En Wang (ORCID: https://orcid.org/0000-0001-7039-0495)
- Patrick J. Walsh (ORCID: https://orcid.org/0000-0001-8392-4150)
- Jianyou Mao (ORCID: https://orcid.org/0000-0003-0581-3978)
- Yuanyun Gu (ORCID: https://orcid.org/0000-0002-7868-0822)
- Dan Xiong (ORCID: https://orcid.org/0000-0003-0722-8668)
- Mingyu Jiang
Institutions
- Hebei Agricultural University (CN)
- Nanjing Tech University (CN)
- University of Pennsylvania (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-05
- DOI
- https://doi.org/10.1021/acs.orglett.4c03492
- Citations
- 2
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangsu Province
- Jiangsu Provincial Key Research and Development Program
- American Chemical Society Petroleum Research Fund
- Division of Chemistry