title: Silver-Catalyzed Isocyanide-Isocyanide [3+2] Cross-Cycloaddition Involving 1,2-Group Migration: Efficient Synthesis of Trisubstituted lmidazoles.
abstract: Imidazole ring is an important five-membered aromatic heterocycle that is widely present in natural products and synthetic molecules. The isocyanide-isocyanide [3+2] cross-cycloaddition reaction constitutes a straightforward method to access imidazoles starting from the easily available chemicals. So far, only three successive reports are known and all lead to the formation of 1,4-disubstituted imidazoles. Here, we report the first isocyanide-isocyanide [3+2] cross-cycloaddition reaction allowing for the formation of 1,4,5-trisubstituted imidazoles under silver catalysis. An unexpected 1,2-migration of sulfonyl, alkoxycaybonyl, and carbamoyl groups took place during the cyclization process that is responsible for the formation of trisubstituted imidazoles. This report displayed a mechanistically novel synthetic method toward a variety of imidazole derivatives, which are otherwise difficult to access by conventional methods.
authors.affiliation: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
authors.forename: Hongwei
authors.initials: H
authors.lastname: Wang
authors.affiliation: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
authors.forename: Rapolu Kiran
authors.initials: RK
authors.lastname: Kumar
authors.affiliation: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yu
authors.affiliation: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
authors.forename: Zhaohong
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
authors.forename: Peiqiu
authors.initials: P
authors.lastname: Liao
authors.affiliation: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China. bixh507@nenu.edu.cn.|State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China. bixh507@nenu.edu.cn.
authors.forename: Xihe
authors.identifier: http://orcid.org/0000-0002-6694-6742
authors.initials: X
authors.lastname: Bi
keywords: 1,2-migration; [3+2] cycloaddition; imidazoles; isocyanides; silver