Abstract
A simple, chemoselective transfer hydrogenation of aryl aldehydes with the aid of Amberlite® resin formate (ARF), a stable H-donor, in the presence of catalytic ruthenium trichloride is described. Aromatic aldehydes and 1,2-diketones are reduced efficiently and selectively, while aryl ketones remain unchanged. Several other potentially reducible groups attached to the aromatic moiety are unaffected.
Highlights
Reduction of carbonyl functionality by transition metal-catalyzed transfer hydrogenation (CTH) with the aid of a suitable hydrogen donor is a valuable synthetic tool and has proved to be a viable alternative to hydrogenation using molecular hydrogen [1,2,3]
We have recently demonstrated that poly-ionic resin formate can act as a stable and potent hydride source in Pd-catalyzed transfer hydrogenation of functionalized alkenes, imines, nitroarenes and 1,2-diketones [23,24]
Our studies reported constitute an efficient method for chemoselective transfer hydrogenation of aryl aldehydes with the aid of resin-supported formate in the presence of catalytic (2.5 mol%) amount of commercially available RuCl3·3H2O in DMF or DMA solution (Scheme 1)
Summary
Reduction of carbonyl functionality by transition metal-catalyzed transfer hydrogenation (CTH) with the aid of a suitable hydrogen donor is a valuable synthetic tool and has proved to be a viable alternative to hydrogenation using molecular hydrogen [1,2,3]. Besides the use of Rh, Ir, Ni and Pd metals in CTH, carbonyl reduction using the combination of Ru(II)-ligand complexes and propan-2-ol in the presence of a base is a widely used method in modern organic synthesis [5]. In the case of CTH, there are some reports on the use of well-defined ortho-metalated and cyclometalated Ru(III) complexes and propan-2-ol (as the hydrogen source) in the presence of a base [16,17,18,19,20], there has been no systematic investigation on the use of RuCl3 in CTH of various organic functional groups
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