A new, palladium-catalyzed synthesis of aromatic mercapturic acid derivatives

Methyl Mercapturate Synthesis: An Efficient, Convenient and Simple Method

“…Finally, our procedure is safe, simple, convenient, and compatible with numerous substrates and, by and large, produced AMEs in higher yields compared to other protocols [ 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ]. Furthermore, availability and low cost of Aliquat 336 are an additional favourable factor to consider.…”

“…While MAs coming from side chain oxidation are well described in the literature [ 19 , 20 , 21 ], MAs resulting from ring oxidation are still being investigated in order to improve their synthesis. Scheme 2 reports the five main procedures for S -arylmercapturic acids (AMA) (or ester derivative) synthesis: the reaction of aryl diazonium salts with cysteine cuprous mercaptides or with N -acetyl- l -cysteine [ 13 , 22 , 23 ], the copper-assisted or palladium-assisted nucleophilic substitution of aryliodides [ 24 , 25 ], the nucleophilic substitution of aryl nitrate or nitroarylhalide [ 26 , 27 , 28 ], a Mitsunobu-type coupling reaction [ 29 ], and finally the process of Behringer et al . [ 30 , 31 ]…”

Preparation of Arylmercapturic Acids by S‐Arylation of N,N′‐Diacetylcystine

“…The procedure described in this paper appears to be, despite the need for an excess of Cu I , more suitable for the preparation of arylmercapturic acids than the catalytic process of Taniguchi 10. It is also a convenient alternative to the Pd‐catalysed arylation of N ‐acetylcysteine by aryl iodides 7a…”

Synthesis of Sulfur-Containing Heterocycles through Oxidative Carbon–Hydrogen Bond Functionalization

“…17 Exposing 9 18 to DDQ provided 2 in 58% isolated yield within 10 min at 0 °C through the same thiocarbenium ion that was formed from allyl sulfide 1 . Vinyl sulfide 10 also proceeded through the oxidative cyclization reaction smoothly, forming 5 with excellent diastereocontrol.…”