Silver(I)‐Catalyzed Widely Applicable Aerobic 1,2‐Diol Oxidative Cleavage

Abstract

The oxidative cleavage of 1,2-diols is afundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage,s uch as H 5 IO 6 ,P b(OAc) 4 ,a nd KMnO 4 ,g enerate stoichiometric hazardous waste.H erein, we describe aw idely applicable and highly selective silver(I)-catalyzed oxidative cleavage of 1,2-diols that consumes atmospheric oxygen as the sole oxidant, thus serving as ap otentially greener alternative to the classical transformations.

Vanadium Catalyst in Micelles: Toward a Greener Aerobic Oxidative Cleavage of Vicinal Diols in Water

“…This important synthetic transformation has historically been performed in organic solvents with stoichiometric amounts of oxidants such as periodates 57 or lead tetra-acetate (Scheme 1a). 58 Transition metal-catalyzed aerobic oxidations (Scheme 1b) have also been reported using cobalt, 59,60 iron, 61,62 manganese, 63−65 nickel, 66 molybdenum, 67 silver, 68,69 cerium, 70 or vanadium complexes. 71−73 Very recently, the aerobic oxidative C−C bond cleavage of vicinal diols in CTABr micellar medium has been reported, using a heterogeneous graphitic carbon nitride photocatalyst.…”

Copper loaded nitrogen-rich mesoporous carbon nitride as a highly efficient photocatalyst for selective oxidative cleavage of C(sp3)–C(sp3) bonds at room temperature under visible light

“…1,2 The synthetic chemistry and petroleum industries have beneted from the selective cleavage and functionalization of this kind of bond. [3][4][5][6] In comparison to the well-developed C(sp 2 )]C(sp 2 ) double bond cleavage and modication process, the cleavage of the C(sp 3 )-C(sp 3 ) single bond and the subsequent functionalization process are also important but have received less attention due to their difficulty and complication. [7][8][9][10][11] Among the diverse methodologies for C-C bond cleavage, we attend to the cleavage of C-C bonds in amines, which has important applications in biomass.…”