Grignard Method for Preparing Thioesters from Esters and Its Application to One-Pot Synthesis of Ketones and Aldehydes
A new protocol for preparing thioesters from the corresponding methyl esters was developed using <sup><i>i</i></sup> PrMgCl and odorless 1-dodecanthiol, <sup><i>n</i></sup> C<sub>12</sub>H<sub>25</sub>SH, under mild reaction conditions, during which in situ-generated C<sub>12</sub>H<sub>25</sub>SMgCl selectively reacted with the carbonyl group of esters. A variety of aromatic and aliphatic esters were readily converted in up to 99% yield with excellent functional group tolerance. Furthermore, based on the quantitative formation of the thioesters, we successfully applied our method to a one-pot synthesis of ketones and aldehydes from esters.
Authors
- Mitsuhiro Arisawa (ORCID: https://orcid.org/0000-0002-7937-670X)
- Kazushi Mashima (ORCID: https://orcid.org/0000-0002-1316-2995)
- Masahiko Seki (ORCID: https://orcid.org/0000-0002-9942-377X)
- Jongseok Kang (ORCID: https://orcid.org/0000-0002-4826-9346)
- Shaheen K. Mulani
- Runlin Yang (ORCID: https://orcid.org/0000-0001-5205-0024)
- Akinari Uchibayashi
Institutions
- Tokuyama (Japan) (JP)
- The University of Osaka (JP)
Publication Details
- Journal
- ACS Omega
- Published
- 2025-02-18
- DOI
- https://doi.org/10.1021/acsomega.4c10622
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Japan Society for the Promotion of Science