Advancing Sustainable Manufacturing through a Heterogeneous Cobalt Catalyst for Selective C–H Oxidation

View Author Information
Department of Chemistry, and School of Forestry and Environmental Studies, Yale University, New Haven, Connecticut United States
Cite this: Ind. Eng. Chem. Res. 2016, 55, 12, 3308–3312
Publication Date (Web):December 8, 2015
https://doi.org/10.1021/acs.iecr.5b03674
Copyright © 2015 American Chemical Society
Article Views
667
Altmetric
-
Citations
LEARN ABOUT THESE METRICS
Read OnlinePDF (288 KB)

Abstract

An increasingly important chemical transformation that will be necessary as we move toward sustainable manufacturing is the oxidation of C–H bonds. Our reported robust heterogeneous cobalt water oxidation catalyst, formed from a metal carbonyl phosphine complex as precursor, is now shown to be active for the selective oxidation of C–H bonds. Of 10 oxidants tested, only Oxone and its oxidatively active component KHSO5 proved competent. A wide variety of substrates were effectively oxidized with KHSO5, including heterocycles, alkyl arenes, alcohols, alkenes, and alkanes. The catalyst is highly selective for C–H bonds over water oxidation when the reaction is conducted in aqueous media. The catalyst can be recycled with minimal loss of activity while under N2. Preliminary mechanistic data are also discussed.

Cited By


This article is cited by 5 publications.

  1. Donghyun Jeong, Jaeheung Cho. Hydride-Transfer Reaction to a Mononuclear Manganese(III) Iodosylarene Complex. Inorganic Chemistry 2021, 60 (11) , 7612-7616. https://doi.org/10.1021/acs.inorgchem.1c00562
  2. Anna Nowacka, Rebecca Vismara, Giorgio Mercuri, Marco Moroni, Miguel Palomino, Kostiantyn V. Domasevitch, Corrado Di Nicola, Claudio Pettinari, Giuliano Giambastiani, Francesc X. Llabrés i Xamena, Simona Galli, Andrea Rossin. Cobalt(II) Bipyrazolate Metal–Organic Frameworks as Heterogeneous Catalysts in Cumene Aerobic Oxidation: A Tag-Dependent Selectivity. Inorganic Chemistry 2020, 59 (12) , 8161-8172. https://doi.org/10.1021/acs.inorgchem.0c00481
  3. Yinlun Huang , Thomas F. Edgar . Preface for the Special Issue on Sustainable Chemical Manufacturing. Industrial & Engineering Chemistry Research 2016, 55 (12) , 3189-3191. https://doi.org/10.1021/acs.iecr.6b01040
  4. Hai-Min Shen, Meng-Yun Hu, Lei Liu, Bei Qi, Hong-Liang Ye, Yuan-Bin She. Efficient and selective oxidation of tertiary benzylic C H bonds with O2 catalyzed by metalloporphyrins under mild and solvent-free conditions. Applied Catalysis A: General 2020, 599 , 117599. https://doi.org/10.1016/j.apcata.2020.117599
  5. Yiwen Yang, Hongxia Ma. Room-temperature direct benzylic oxidation catalyzed by cobalt(II) perchlorate. Tetrahedron Letters 2016, 57 (47) , 5278-5280. https://doi.org/10.1016/j.tetlet.2016.10.049