Electrocatalytic reduction of benzoylformic acid mediated by methyl viologen

Organic Reactions Mediated by Cyclodextrins

“…In the presence of β-CD or mono-6-deoxy-6-[N-(2-aminoethyl)]amino-β-CD (β-CDen), BFA was reduced electrocatalytically with methyl viologen (MV 2+ ), the two-electron reduction product of which behaves as the active reductant, with excellent yields (99%) and enentioselectivity, 14% ee (S) and 19% (S), respectively. 84 A mechanism was not proposed. However, it has been reported that β-CD included methyl viologen 85 in a 1:1 stoichiometry as well as MV bound more strongly than either MV + or MV 2+ to β-CD.…”

“…CD also can mediate electrochemical reduction reactions. In the presence of β-CD or mono-6-deoxy-6-[ N -(2-aminoethyl)]amino-β-CD (β-CDen), BFA was reduced electrocatalytically with methyl viologen (MV 2+ ), the two-electron reduction product of which behaves as the active reductant, with excellent yields (99%) and enentioselectivity, 14% ee ( S ) and 19% ( S ), respectively . A mechanism was not proposed.…”

Recent Advances in Asymmetric Catalytic Electrosynthesis

“…The transformation resulted in only modest chiral induction and moderate yields, the latter due to competing dimerization of the intermediate coumarin radical. Nevertheless, the organocatalytic strategy inspired the work of other groups working in this field [81][82][83] and chiral amines have been used as additives in catalytic amounts for asymmetric reduction of various ketones, carboxylic acids and oximes as well as for reductive dehalogenation [84][85][86][87][88][89][90][91][92][93][94][95][96][97]. Electrocatalytic reductions have also been carried out using metal catalysts, including a Rh III polypyridyl complex for the hydrogenation of acetophenone with modest chiral induction [98].…”

Asymmetric Electrochemical Catalysis

“…In 1995, Park et al. reported an asymmetric reduction of a ketoacid by β‐cyclodextrin . By employing methyl viologen as a mediator, the reduction process showed 14 % ee (Scheme ).…”

“…[26] In 1995, Park et al reported an asymmetricr eduction of ak etoacid by b-cyclodextrin. [27] By employing methyl viologen as am ediator,t he reduction process showed1 4% ee (Scheme1 1). Later in 2008, Pilli and Santo also used b-cyclodextrin as co-catalyst in the oxidative cyanation reaction of piperidine with 65 % yield and 30 % ee (Scheme 11).…”