Abstract
Sulfones are building blocks in organic synthesis and pharmaceutical chemistry. Direct α-alkylation of sulfones using alcohols with water as the sole byproduct is an efficient and promising method for their structural modifications. However, competitive reactions always exist in this transformation that influences the reaction selectivity. For example, in addition to the desired α-alkylation, Julia-type olefination and α-alkenylation are frequently observed, especially when benzyl alcohol derivatives were used as alkylation reagents. Herein, we report α-alkylation of sulfones using alcohols catalyzed by a pincer complex of earth-abundant manganese. The Mn-PNN-bipyridyl complex exhibited good performance in reaction selectivity. The amount of base also had an important influence on the smooth transformation. Aromatic and aliphatic alcohols are suitable alkylation reagents for sulfones at low metal catalyst loading (0.5 mol %), highlighting the practicality of the developed system.
| Original language | English |
|---|---|
| Pages (from-to) | 5949-5954 |
| Number of pages | 6 |
| Journal | ACS Catalysis |
| Volume | 13 |
| Issue number | 9 |
| Early online date | 17 Apr 2023 |
| DOIs | |
| Publication status | Published - 5 May 2023 |
Funding
L.L. is thankful to the Feinberg Graduate School (FGS) of the Weizmann Institute of Science for a Dean Excellence Postdoc Fellowship, and J.L. is thankful to the FGS for a Senior Postdoctoral Fellowship. Author contributions - D.M. and L.L. conceived and directed the project and designed the experiments. L.L. performed and analyzed the experiments. J.L. provided insightful discussions. All authors were involved in manuscript preparation.
All Science Journal Classification (ASJC) codes
- Catalysis
- General Chemistry