由酯制备硫酯的格氏方法及其在酮和醛一锅法合成中的应用。
Grignard Method for Preparing Thioesters from Esters and Its Application to One-Pot Synthesis of Ketones and Aldehydes.
作者信息
Mulani Shaheen K, Kang Jiaao, Yang Runlin, Uchibayashi Akinari, Arisawa Mitsuhiro, Seki Masahiko, Mashima Kazushi
机构信息
Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.
R&D Planning Department, Tokuyama Corporation, Tsukuba 300-4247, Japan.
出版信息
ACS Omega. 2025 Feb 18;10(8):8462-8471. doi: 10.1021/acsomega.4c10622. eCollection 2025 Mar 4.
A new protocol for preparing thioesters from the corresponding methyl esters was developed using PrMgCl and odorless 1-dodecanthiol, CHSH, under mild reaction conditions, during which in situ-generated CHSMgCl 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.
利用PrMgCl和无臭的1-十二烷硫醇（CHSH），在温和的反应条件下，开发了一种从相应甲酯制备硫酯的新方案。在此过程中，原位生成的CHSMgCl与酯的羰基选择性反应。各种芳香族和脂肪族酯很容易以高达99%的产率转化，且对官能团具有出色的耐受性。此外，基于硫酯的定量形成，我们成功地将我们的方法应用于从酯一锅合成酮和醛。
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