Green Organocatalytic Dihydroxylation of Alkenes

Abstract

An inexpensive, green, metal‐free one‐pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2‐trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.

Green Organocatalytic Oxidative Methods using Activated Ketones

“…In the first step, the olefinic group is epoxidized, and subsequently, the functional group attacks the ring and opens the epoxide to afford the desired cyclized product, with or without the use of a suitable additive (Schemes and ). Another application of the green organocatalytic protocol is the synthesis of polyalcohols from alkenes . Triols are moieties that are embedded in numerous natural products and compounds with biological properties, including bengazole A and ceramide sphingolipid (Scheme )…”

“…Another application of the green organocatalytic protocol is the synthesis of polyalcohols from alkenes. [106] Triols are moieties that are embedded in numerous naturalp roducts and compounds with biological properties, including bengazole A [107] and ceramide sphingolipid (Scheme 30). [108] Starting from av ariety of homoallylic alcohols and aminoalkenes,p olyalcohols can be obtainedi ne xcellent yields.…”

Magnetically separable and reusable rGO/Fe3O4 nanocomposites for the selective liquid phase oxidation of cyclohexene to 1,2-cyclohexane diol

“…[20][21][22] The H 2 O 2 assisted cyclohexene oxidation to 1,2-diol in a catalytic route has been also reported over a set of homogeneous and heterogeneous catalysts. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] For example, Usui et al 26 reported a maximum diol yield of 98% in a solvent-and metal-free cyclohexene oxidation using H 2 O 2 , catalyzed by immobilized sulfonic acids. In another work, Rosatella et al 27 reported the application of Brønsted acids in the catalytic conversion of cyclohexene to diol.…”

“…Among the various catalysts used the para-toluene sulfonic acid was found to be showing the highest diol yield of 98%. Theodorou et al 28 used 2,2,2-triuoroacetophenone as an organocatalyst for the oxidation of cyclohexene to diol using H 2 O 2 and nearly 96% yield was observed for the product. Yu et al 29,30 reported the use of organoselenium compounds for the selective oxidation of cyclohexene to diol using H 2 O 2 as the oxidant.…”

Characterization and flocculation evaluation of a new organic–inorganic hybrid polymer flocculant (PAC‐AM‐DMC)

“…[10][11][12] Among them, the physical method mainly targets the suspended solids in the sewage, the chemical method targets the colloidal particles and soluble substances in the sewage, and the biodegradation method primarily relies on the degradation of microorganisms to purify the sewage. [13][14][15] The coagulation method combined the physical and chemical treatment methods, which is currently recognized as the best economic effect and treatment effect.…”