Selective reduction of mono- and disubstituted olefins by NaBH4 and catalytic RuCl3

Stereoselective Synthesis of Chiral Polycyclic Indolic Architectures through Pd0‐Catalyzed Tandem Deprotection/Cyclization of Tetrahydro‐β‐carbolines on Allenes

“…In an effort to avoid the troublesome purification of the diastereoisomeric mixtures, it was envisaged to submit the crude cyclization mixtures to a reduction step of the double bonds to simplify the purification of the compounds. Accordingly, the crude mixtures resulting from the palladium‐catalyzed reactions were submitted to NaBH 4 , in the presence of a catalytic amount of RuCl 3 (Scheme , step 2) 35. We found that a short purification to remove the DMBA derivatives was necessary prior to the reduction step.…”

“…Eur.J.2015, 21,8511-8520 www.chemeurj.org ingly,t he crude mixtures resulting from the palladium-catalyzed reactions were submitted to NaBH 4 ,i nt he presence of ac atalytic amount of RuCl 3 (Scheme 7, step 2). [35] We found that as hort purificationt or emove the DMBA derivatives was necessary prior to the reduction step. The reductions were then performed only on the cis diastereoisomers 18 a,b and 20 a,b.…”

Ruthenium nanoparticle-intercalated montmorillonite clay for solvent-free alkene hydrogenation reaction

“…Both theoretical and experimental values were found to be in good agreement, and 2.5 wt% Ru MMT. [22] This protocol also minimizes the loss of Ru nanoparticles during the synthesis of Ru MMT.…”

“…[16][17][18][19][20][21] Several hydrogenating reagents such as NiCl 2 -NaBH 4 , PdCl 2 -NaBH 4 polyethylene glycol (PEG)-CH 2 Cl 2 , CoCl 2 -NaBH 4 etc., have been tested as hydrogenation systems. [22] Along with toxicity, these systems also suffered with long reaction time, high catalyst loading, costly starting materials and tedious reaction protocol of these hydrogenating reagents.…”

Sodium Borohydride

“…Various unactivated mono-or disubstituted olefins and activated trisubstituted olefins were reduced with RuCl 3 (10 mol %) and NaBH 4 in THF-H 2 O at 0 • C to room temperature (eq 36). 163 When the RuCl 3 -catalyzed reductions of olefins were carried out in aqueous amide solution, unactivated trisubstituted olefins were also hydrogenated. 164 (36) Deoxygenation of sulfoxides by NaBH 4 is effected by the combination of CoCl 2 ·6H 2 O and moist alumina in hexane (eq 37).…”