Detailed Information

Cited 0 time in webofscience Cited 0 time in scopus
Metadata Downloads

Significant facilitation of metal-free aerobic oxidative cyclization of imines with water in synthesis of benzimidazoles

Authors
Lee, Ye-SolCho, Yeon-HoLee, SeungJaeBin, Jong-KwanYang, JoongHwanChae, GeeSungCheon, Cheol-Hong
Issue Date
28-1월-2015
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Keywords
Benzimidazole; Aerobic oxidation; Metal-free; Nucleophilic catalyst; Water; Baldwin' s rules
Citation
TETRAHEDRON, v.71, no.4, pp.532 - 538
Indexed
SCIE
SCOPUS
Journal Title
TETRAHEDRON
Volume
71
Number
4
Start Page
532
End Page
538
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/94606
DOI
10.1016/j.tet.2014.12.043
ISSN
0040-4020
Abstract
A simple, convenient, and environmentally benign protocol for the synthesis of benzimidazoles from ortho-phenylenediamines and aldehydes via aerobic oxidation was developed in wet organic solvents. Notably, water significantly accelerated this transformation, which allowed us to achieve this important transformation without the assistance of any metal catalysts and other co-oxidants. Mechanistic studies suggested that water acts as the nucleophilic catalyst for this transformation by the conversion of dis-favored 5-endo-trig cyclization of imines to favored 5-exo-tet cyclization via tetrahedral intermediates and the subsequent aerobic oxidation of the resulting benzimidazolines affords benzimidazoles. (C) 2014 Elsevier Ltd. All rights reserved.
Files in This Item
There are no files associated with this item.
Appears in
Collections
College of Science > Department of Chemistry > 1. Journal Articles

qrcode

Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.

Altmetrics

Total Views & Downloads

BROWSE