Iridium-catalyzed intramolecular CN and CO/S cross-coupling reactions: Preparation of benzoazole derivatives. Issue 40 (3rd October 2019)

• Record Type: Journal Article
• Authors: Shi, Yajie; Zhou, Qifan; Du, Fangyu; Fu, Yang; Du, Yang; Fang, Ting; Chen, Guoliang
• Is Part Of: Tetrahedron letters. Volume 60:Issue 40(2019)
• Publication Date: 2019-10-03
• Subjects: Iridium -- Catalysis -- Intramolecular cross-coupling -- Benzoazole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151082
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Iridium can catalyzed intramolecular CN and CO/S cross-coupling reactions. Benzoazole derivatives are readily available using this method. Iridium catalyst can be effective with just 1 mol% catalyst loading. Iridium performs better with low reactivity substrates than Cu or Pd. One drug was prepared using this method. Abstract: The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o -haloarylamides or o -haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.