Kaur Arshpreet, Pannu Arshdeep, Brar Deshkanwar S, Mehta Surinder K, Salunke Deepak B
Department of Chemistry and Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India.
National Interdisciplinary Centre of Vaccines, Immunotherapeutics and Antimicrobials, Panjab University, Chandigarh 160014, India.
ACS Omega. 2020 Aug 13;5(33):21007-21014. doi: 10.1021/acsomega.0c02516. eCollection 2020 Aug 25.
Protecting group chemistry has invariably captured the fascination of chemists because of its extensive viability in chemical synthesis. The present report describes our pioneer work of applying ytterbium triflate as a catalyst, for the reaction of alcohols with di--butyl dicarbonate (BocO) leading to the formation of -butyl ethers. There exists no recorded evidence for the use of Yb(OTf) as a catalyst for the protection of alcohols to -butyl ethers, despite its excellent utility in various reactions. Yb(OTf) has been used predominantly in the catalytic deprotection studies such as selective deprotection of -butyl esters to carboxylic acids as well as prenyl ethers to alcohols. This study involved the critical evaluation of solvent, time, and temperature that finally led to an efficient protocol for the formation of -butyl ethers. Yb(OTf) catalyzed the formation of -butyl ethers, notably reducing the reaction time, which is exemplified by the achievement of up to 92% conversion of alcohols to -butyl ethers within an hour. Additionally, the report demonstrates the utility of this synthetic protocol for the protection of carboxylic acids.
保护基团化学因其在化学合成中广泛的适用性，一直吸引着化学家们。本报告描述了我们开创性的工作，即应用三氟甲磺酸镱作为催化剂，使醇类与二碳酸二叔丁酯（BocO）反应生成叔丁基醚。尽管三氟甲磺酸镱（Yb(OTf)）在各种反应中具有出色的效用，但尚无将其用作催化剂将醇类保护为叔丁基醚的记录证据。Yb(OTf)主要用于催化脱保护研究，如将叔丁基酯选择性脱保护为羧酸以及将异戊烯基醚脱保护为醇类。本研究涉及对溶剂、时间和温度的关键评估，最终形成了一种高效的叔丁基醚形成方案。Yb(OTf)催化叔丁基醚的形成，显著缩短了反应时间，例如在一小时内醇类转化为叔丁基醚的转化率高达92%。此外，该报告还展示了这种合成方案在保护羧酸方面的效用。
