Literature DB >> 25761008

Bioinspired organocatalytic aerobic C-H oxidation of amines with an ortho-quinone catalyst.

Yan Qin1, Long Zhang1,2, Jian Lv1,2, Sanzhong Luo1,2, Jin-Pei Cheng1,2.   

Abstract

A simple bioinspired ortho-quinone catalyst for the aerobic oxidative dehydrogenation of amines to imines is reported. Without any metal cocatalysts, the identified optimal ortho-quinone catalyst enables the oxidations of α-branched primary amines and cyclic secondary amines. Mechanistic studies have disclosed the origins of different performances of ortho-quinone vs para-quinone in biomimetic amine oxidations.

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Year:  2015        PMID： 25761008     DOI： 10.1021/acs.orglett.5b00351

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates.

Authors:  Bao Li; Alison E Wendlandt; Shannon S Stahl
Journal:  Org Lett       Date:  2019-01-31       Impact factor: 6.005

2.  Quinone 1 e- and 2 e-/2 H+ Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships.

Authors:  Mioy T Huynh; Colin W Anson; Andrew C Cavell; Shannon S Stahl; Sharon Hammes-Schiffer
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

Review 3.  Quinone-Catalyzed Selective Oxidation of Organic Molecules.

Authors:  Alison E Wendlandt; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-04       Impact factor: 15.336

4.  A bioinspired catalytic aerobic oxidative C-H functionalization of primary aliphatic amines: synthesis of 1,2-disubstituted benzimidazoles.

Authors:  Khac Minh Huy Nguyen; Martine Largeron
Journal:  Chemistry       Date:  2015-07-23       Impact factor: 5.236

5.  Three-Component Reaction of Benzylamines, Diethyl Phosphite and Triethyl Orthoformate: Dependence of the Reaction Course on the Structural Features of the Substrates and Reaction Conditions.

Authors:  Patrycja Miszczyk; Ilona Turowska-Tyrk; Paweł Kafarski; Ewa Chmielewska
Journal:  Molecules       Date:  2017-03-11       Impact factor: 4.411

6.  Redox-Active Guanidines in Proton-Coupled Electron-Transfer Reactions: Real Alternatives to Benzoquinones?

Authors:  Ute Wild; Olaf Hübner; Hans-Jörg Himmel
Journal:  Chemistry       Date:  2019-09-19       Impact factor: 5.236

7.  Modification of N-terminal α-amine of proteins via biomimetic ortho-quinone-mediated oxidation.

Authors:  Siyao Wang; Qingqing Zhou; Xiaoping Chen; Rong-Hua Luo; Yunxue Li; Xinliang Liu; Liu-Meng Yang; Yong-Tang Zheng; Ping Wang
Journal:  Nat Commun       Date:  2021-04-15       Impact factor: 14.919

8.  Excellent Catalytic Performances of a Au/C-CuO Binary System in the Selective Oxidation of Benzylamines to Imines under Atmospheric Oxygen.

Authors:  Yuki Yamamoto; Miyuto Ota; Shintaro Kodama; Michio Ueshima; Akihiro Nomoto; Akiya Ogawa; Mitsunori Furuya; Kiminori Kawakami
Journal:  ACS Omega       Date:  2021-12-06

Review 9.  Oxidative dehydrogenation of C-C and C-N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds.

Authors:  Santanu Hati; Ulrike Holzgrabe; Subhabrata Sen
Journal:  Beilstein J Org Chem       Date:  2017-08-15       Impact factor: 2.883

10.  Bio-inspired lanthanum-ortho-quinone catalysis for aerobic alcohol oxidation: semi-quinone anionic radical as redox ligand.

Authors:  Ruipu Zhang; Runze Zhang; Ruijun Jian; Long Zhang; Ming-Tian Zhang; Yu Xia; Sanzhong Luo
Journal:  Nat Commun       Date:  2022-01-20       Impact factor: 17.694
  10 in total

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