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      One-Pot Multicomponent Coupling Reaction of Catechols, Benzyl Alcohols/Benzyl Methyl Ethers, and Ammonium Acetate toward Synthesis of Benzoxazoles

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      Author(s): , ,
      Publication date (Electronic):
      Journal: ACS Omega
      Publisher: American Chemical Society

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          Abstract

          The multicomponent coupling reaction of catechol, ammonium acetate, and benzyl alcohol/benzyl methyl ether in the presence of a Fe(III) catalyst precursor afforded benzoxazole derivatives in good to excellent yields. The notable features of this protocol are abundant availability of the catalyst system, large-scale synthesis, high diversity, and high yields of products.

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          Iron catalysis in organic synthesis.

          Ingmar Bauer, Hans-Joachim Knölker (2015)
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            Iron(iii) chloride in oxidative C–C coupling reactions

            Abdelwareth Sarhan, Carsten Bolm (2009)
            In this critical review, the use of iron(III) chloride in oxidative C-C couplings of arenes and related unsaturated compounds is presented and reviewed. The approach allows highly selective dimerisations of phenol derivatives, naphthols, and heterocyclic compounds. Sequential couplings give access to structurally well-defined oligo- and polymers. Iron(III) chloride is commercially available and inexpensive. Being a mild oxidising agent it has been applied in numerous reactions leading to new carbon-carbon-bonds in complex molecular arrays (107 references).
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              Discovery of a Metalloenzyme-like Cooperative Catalytic System of Metal Nanoclusters and Catechol Derivatives for the Aerobic Oxidation of Amines

              Hao Yuan, Hiroyuki Miyamura, Shu̅ Kobayashi … (2012)
              We have discovered a new class of cooperative catalytic system, consisting of heterogeneous polymer-immobilized bimetallic Pt/Ir alloyed nanoclusters (NCs) and 4-tert-butylcatechol, for the aerobic oxidation of amines to imines under ambient conditions. After optimization, the desired imines were obtained in good to excellent yields with broad substrate scope. The reaction rate was determined to be first-order with respect to the substrate and catechol and zero-order for the alloyed Pt/Ir NC catalyst. Control studies revealed that both the heterogeneous NC catalyst and 4-tert-butylcatechol are essential and act cooperatively to facilitate the aerobic oxidation under mild conditions.
              Article 0 comments Cited 40 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Omega
                Journal ID (iso-abbrev): ACS Omega
                Journal ID (publisher-id): ao
                Journal ID (coden): acsodf
                Title: ACS Omega
                Publisher: American Chemical Society
                ISSN (Electronic): 2470-1343
                Publication date (Electronic): 18 August 2021
                Publication date Collection: 31 August 2021
                Volume: 6
                Issue: 34
                Pages: 22395-22399
                Affiliations
                [1]Department of Chemistry, College of Sciences, Shiraz University , Shiraz 71454, Iran
                Author notes
                [* ]Email: Panahi@ 123456shirazu.ac.ir . Tel.: (+98)7136137136. Fax: (+98)7132280926.
                Author information
                https://orcid.org/0000-0003-0420-4409
                https://orcid.org/0000-0001-6772-3332
                Article
                DOI: 10.1021/acsomega.1c03207
                PMC ID: 8412954
                PubMed ID: 34497928
                SO-VID: e7581692-60b4-4a25-9c1c-00de1286c9e3
                Copyright © © 2021 The Authors. Published by American Chemical Society
                License:

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                Date received : 20 June 2021
                Date accepted : 06 August 2021
                Funding
                Funded by: Shiraz University, doi 10.13039/501100005071;
                Award ID: NA
                Funded by: Iran Science Elites Federation, doi 10.13039/501100018981;
                Award ID: NA
                Categories
                Subject: Article
                Custom metadata
                document-id-old-9 ao1c03207
                document-id-new-14 ao1c03207
                ccc-price

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