Heterogeneous Sodium-Manganese Oxide Catalyzed Aerobic Oxidative Cleavage of 1,2-Diols. 2017

Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
Center for Green Chemistry & Green Engineering, Yale University, New Haven, CT, 06520, USA.

The aerobic oxidative cleavage of 1,2-diols using a heterogeneous catalyst only based on earth-abundant metals manganese and sodium is reported for the first time. This reusable catalyst cleaves a variety of substrates into aldehydes or ketones with high selectivity. The reaction requires small catalytic loadings and is performed under mild conditions using ambient pressure O2 or air as the oxidant while producing water as the only by-product. Mechanistic investigations reveal a monodentate, two-electron oxidative fragmentation process involving a MnIV species. The eco-friendly, innocuous catalyst is compatible with a wide range of functional groups and conditions, making it highly competitive with classical reagents, such as periodic acid or lead tetraacetate, as a preferred method for activated 1,2-diols.

UI MeSH Term Description Entries

Related Publications

Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
October 2020, ChemSusChem,
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
March 2018, Angewandte Chemie (International ed. in English),
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
May 2023, Organic & biomolecular chemistry,
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
February 2011, Chemistry, an Asian journal,
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
February 2016, Angewandte Chemie (International ed. in English),
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
February 2017, Chemical communications (Cambridge, England),
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
April 2005, Journal of the American Chemical Society,
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
March 2015, Journal of the American Chemical Society,
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
June 2021, The Journal of organic chemistry,
Vincent Escande, and Chun Ho Lam, and Philip Coish, and Paul T Anastas
June 2011, The Journal of organic chemistry,
Copied contents to your clipboard!