Construction of a Clock Catalytic System: Highly Efficient and Self-Indicating Synthesis of Benzoheterocycles at Ambient Temperature

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First Author:Xiong, Wu-Lin

Correspondence Author:Sun, Hong-bin Sun, Qi

Co author:Peng, Xiao-Chong Zhong, Ren-Yuan Zheng, Jianwei Duo, Shuwang Gong, Shan-Shan

Journal:Asian Journal of Organic Chemistry

Issue:12

Volume:10

Impact Factor:2.8

DOI number:10.1002/ajoc.202100508

Affiliation of Author(s):Department of Chemistry, Northeastern University

Teaching and Research Group:物理化学

Place of Publication:UNITED STATES

Abstract:Inspired by the mechanism of the clock reaction, we rationally constructed a novel phosphomolybdenum blue (PMB) clock catalytic system for a highly efficient synthesis of benzimidazoles and benzothiazoles simply at ambient temperature. The current PMB clock catalytic system exhibits a sharp decoloration event to announce the depletion of the intermediateconstraint, making this synthetic approach self-indicating and TLC-free.P-31 NMR and XPS analysis of PMBcatalyst showed that only two Mo6+ atoms are reduced to Mo5+ atoms in the Keggin structure due to the moderate reducibility of benzimidazoline and benzothiazoline intermediates. Thus,the active Keggin-type POM cluster could be well maintained in DMSO during the redox cycling of phosphomolybdic acid (PMA) and PMB. H-1 NMR tracing experiment not only confirmed the proposed reaction mechanism but also showed that PMB exerts Lewis acid catalytic activityat the early phase of the reaction other than the expected redox catalytic activity.

Document Code:WOS:000711547600001

Discipline:Natural Science

First-Level Discipline:Chemistry

Page Number:3321-3327

ISSN No.:2193-5807

Translation or Not:no