Ghorai Sourav, Lin Yongjia, Xia Yuanzhi, Wink Donald J, Lee Daesung
Department of Chemistry , University of Illinois at Chicago , 845 West Taylor Street , Chicago , Illinois 60607 , United States.
College of Chemistry and Materials Engineering , Wenzhou University , Wenzhou , Zhejiang Province 325035 , P. R. China.
Org Lett. 2020 Jan 17;22(2):642-647. doi: 10.1021/acs.orglett.9b04416. Epub 2019 Dec 31.
Pathway selective aryne-based novel multicomponent coupling reactions with isonitriles and nitriles are described. Crucial to these reactions is the formation of a silver-aryne complex, which shows differential reactivity toward isonitriles and nitriles to form two different forms of -nitrilium organosilver arene species. Interception of the nitrilium of an aryne-isonitrile adduct with another isonitrile leads to the formation of benzocyclobutene-1,2-diimines, whereas the nitrilium of an aryne-nitrile adduct renders selective formation of 3-indol-3-imines or 3-iminoindolin-2-ol depending on the structure of the nitrile employed.
描述了基于芳炔与异腈和腈的新型多组分偶联反应的途径选择性。这些反应的关键是形成银-芳炔配合物，该配合物对异腈和腈表现出不同的反应性，以形成两种不同形式的腈鎓有机银芳烃物种。芳炔-异腈加合物的腈鎓与另一种异腈的截获导致苯并环丁烯-1,2-二亚胺的形成，而芳炔-腈加合物的腈鎓根据所用腈的结构选择性地形成3-吲哚-3-亚胺或3-亚氨基吲哚啉-2-醇。
