文献类型：期刊文献

英文题名：Concise Synthesis of Chromene/Chromane-Type Aryne Precursors and Their Applications

作者：Xu, Yuan-Ze[1,2];Tian, Jia-Wei[1,2];Sha, Feng[1,2];Li, Qiong[1,2];Wu, Xin-Yan[1,2]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2021

卷号：86

期号：9

起止页码：6765

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20211810307190);WOS:【SCI-EXPANDED(收录号:WOS:000649101400063)】；

基金：The authors are grateful for financial support from the Shanghai Pujiang Program (18PJD010), the Natural Science Foundation of Shanghai (19ZR1412300), and the Fundamental Research Funds for the Central Universities (222201814019). The authors thank Ms. Feng Qian at Research Center of Analysis and Test of East China University of Science and Technology for help with HRMS-EI analysis.

语种：英文

外文关键词：Cycloaddition - Addition reactions

摘要：The gram-scale synthesis of 5,6-, 6,7-, and 7,8-chromene/chromane-type aryne precursors and their applications in regioselective transformation to other functional derivatives is reported. Chromene/chromane-type arynes are generated under mild conditions, which can further undergo [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions, nucleophilic addition reactions, and a-insertion reactions to produce structurally novel substituted chromenes and chromanes. The excellent regioselectivity of the reaction is facilitated by the oxygen-containing guiding groups at the ortho-position of the triple bond, which can be removed or switched to other functional groups including alkenyl, aryl, heteroaryl, and arylamino groups.