利用 Selectfluor 实现 3-甲基香豆素的 C(sp3)-H 烷氧基化反应。

Selectfluor-Enabled C(sp)-H Alkoxylation of 3-Methylfuranocoumarins.

机构信息

Department of Organic Chemistry, College of Chemistry, Jilin University, Jiefang Road 2519, Changchun 130023, China.

Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599, United States.

出版信息

J Org Chem. 2021 Jun 4;86(11):7864-7871. doi: 10.1021/acs.joc.1c00776. Epub 2021 May 25.

DOI:10.1021/acs.joc.1c00776

PMID:34033489

Abstract

A facile and metal-free method for the direct C(sp)-H bond alkoxylation of 3-methylfuranocoumarins with alcohols has been disclosed. Selectfluor enabled the (hetero)benzylic C-H etherification by tuning the reaction temperature and solvent. Various alcohols were compatible in this transformation with suitable yields. The mechanistic studies revealed that the reaction might undergo the double addition process of alcohols, as well as the departure of a fluoride anion and the formation of an oxonium ion.

摘要

本文报道了一种简便、无需金属的方法，可实现 3-甲基呋喃香豆素与醇的直接 C(sp 3 )-H 键烷氧基化反应。通过调节反应温度和溶剂，Selectfluor 可实现（杂）苄基 C-H 醚化。该转化中各种醇都具有良好的兼容性，产率合适。机理研究表明，反应可能经历了醇的双加成过程，以及氟阴离子的离去和氧翁离子的形成。