N-tert-Butylbenzenesulfenamide-catalyzed oxidation of alcohols to the corresponding carbonyl compounds with N-chlorosuccinimide

A Simple and Highly Selective Biomimetic Oxidation of Alcohols and Epoxides with N‐Bromosuccinimide in the Presence of β‐Cyclodextrin in Water

“…Cyclodextrin has also been recovered and reused. In the case of epoxycinnamyl alcohol (Entry 21) also the product obtained in dichloromethane (in the absence of b-CD) was only the aldehyde by the oxidation of the primary alcohol retaining the oxirane as observed by Mukaiyama et al, [7] whereas in the presence of b-CD in water the a-hydroxyketone was obtained as the product. When a catalytic amount of cyclodextrin (0.1 mmol per 1 mmol of substrate) was used the reaction with alcohols did not go to completion and the product formation was only to the extent of 40 ± 50% under the reported reaction conditions.…”

“…However, even catalytic oxidations have some limitations such as pH of the medium, controlled temperature, hazardous reagents and solvents, formation of side products etc. [6,7] The N-bromosuccinimide (NBS) oxidations of alcohols reported are usually carried out using either anhydrous solvents or in acidic or basic media at varied temperatures. The selectivities observed were also not encouraging in some cases.…”

Catalytic Oxidative Processes in Steroid Chemistry: Allylic Oxidation, β-Selective Epoxidation, Alcohol Oxidation and Remote Functionalization Reactions

“…The same oxidant was used in the conversion of 17 -methylandrostane-3 ,17 -diol 64 to the corresponding 3-keto derivative 65 catalyzed by sodium tungstate, under phase transfer conditions (scheme 14) [139h]. N-tertButylbenzenesulfenamide catalyzed the oxidation of 5 -lanosta-8,24-dien-3 -ol 66 to the corresponding 3-ketone 67 using N-chlorosuccinimide in the presence of K 2 CO 3 and MS 4Å at temperatures ranging from 0ºC to room temperature (scheme 15) [165].…”

“…13, scheme 20) [162]. N-tert-Butylbenzenesulfenamide catalyzed the oxidation of 17 -hydroxy-5 -androstan-3-one 75 to the corresponding 17-ketone 55 (scheme 19) using N-chlorosuccinimide in the presence of K 2 CO 3 and MS 4Å [165]. Testosterone 72 (scheme 18) and 17 -hydroxy-5 -androstan-3-one 75 …”

Efficient Oxidation of Benzylic Alcohols to Aldehydes and Ketones in Ionic Liquid Using N-Chlorosuccinimide/AlCl3.6H2O

“…17 Use of N-chlorosuccinimide in oxidation reactions are highly promising due to its ready availability, ease of manipulation, and less toxic nature. However, reported NCS induced oxidation methods invariably utilized bases such as K 2 CO 3 , 18 EtN(i-Pr) 2 , 19 and NaHCO 3 . 20 Therefore, it is highly desirable to develop the NCS promoted oxidation procedure of benzylic alcohols avoiding use of basic reaction conditions.…”