Premium
Heterogeneous Sodium‐Manganese Oxide Catalyzed Aerobic Oxidative Cleavage of 1,2‐Diols
Author(s) -
Escande Vincent,
Lam Chun Ho,
Coish Philip,
Anastas Paul T.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705934
Subject(s) - catalysis , chemistry , manganese , oxidative cleavage , reagent , heterogeneous catalysis , selectivity , denticity , oxidative phosphorylation , inorganic chemistry , bond cleavage , combinatorial chemistry , organic chemistry , metal , photochemistry , biochemistry
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 O 2 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 Mn IV 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.