Ghorai Sourav, Lee Daesung
Department of Chemistry , University of Illinois at Chicago , 845 West Taylor Street , Chicago , Illinois 60607 , United States.
Org Lett. 2019 Sep 20;21(18):7390-7393. doi: 10.1021/acs.orglett.9b02711. Epub 2019 Sep 4.
New aryne-based multicomponent coupling reactions for the formation of functionalized aromatic compounds have been developed. Arynes generated from triynes or tetraynes through the hexadehydro Diels-Alder reaction readily react with isocyanide to generate nitrilium intermediate. Intercepting this nitrilium species with various weak nucleophile including carboxylic acids, alcohols, sulfonamides, or water generated the corresponding imides, imidates, amidines, or amides. The high regioselectivity of these transformations was mainly controlled by the substituents of the arynes.
已开发出用于形成功能化芳香族化合物的基于新芳炔的多组分偶联反应。通过六脱氢狄尔斯-阿尔德反应从三炔或四炔生成的芳炔很容易与异腈反应生成腈鎓中间体。用包括羧酸、醇、磺酰胺或水在内的各种弱亲核试剂捕获该腈鎓物种，生成相应的酰亚胺、亚胺酸酯、脒或酰胺。这些转化的高区域选择性主要由芳炔的取代基控制。
