B <sub>2</sub> Pin <sub>2</sub> -enabled reductive thioesterification of aryl triflates with thiocarbonates
In this work, we demonstrate a B<sub>2</sub>Pin<sub>2</sub>-mediated reductive coupling of aryl triflates with thiocarbonates for aryl thioester synthesis. This method surpasses previous Zn-based protocols, especially for pyridyl and sterically hindered 2,6-disubstituted arenes, likely due to distinct reduction pathways. Its utility is demonstrated in the thioesterification of pharmaceuticals (apixaban, ezetimibe, ethinyl estradiol derivatives) under mild conditions. Furthermore, this work lays the foundation for B<sub>2</sub>Pin<sub>2</sub>-driven reductive C(sp<sup>2</sup>)-C(sp<sup>2</sup>) couplings using earth-abundant metals, offering a scalable alternative to traditional Zn/Mn reductants in industrial settings.
Authors
- Hegui Gong (ORCID: https://orcid.org/0000-0001-6534-5569)
- Shaojie Xu (ORCID: https://orcid.org/0000-0002-0773-925X)
- Houguang Shi
- Xiaotai Wang (ORCID: https://orcid.org/0000-0003-3310-3308)
- Fan Wu (ORCID: https://orcid.org/0000-0002-0495-6814)
- Wei Zhu (ORCID: https://orcid.org/0000-0001-7190-7476)
- Hong C. Shen (ORCID: https://orcid.org/0000-0002-3477-8932)
Institutions
- Ningbo University (CN)
- Shanghai University (CN)
- Roche (China) (CN)
- Xi’an Jiaotong-Liverpool University (CN)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc04038h
- Primary Topic
- Chemical Synthesis and Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00