54769-59-4Relevant articles and documents
A Route to O-Aminosulfonates and Sulfonamides through Insertion of Sulfur Dioxide and Hydrogen Atom Transfer
Liu, Tong,Zheng, Danqing,Li, Zhenhua,Wu, Jie
supporting information, p. 2653 - 2659 (2017/08/16)
A three-component reaction of aryldiazonium tetrafluoroborates, the 1,4-diazabicyclo[2.2.2]octane?bis(sulfur dioxide) adduct [DABCO?(SO2)2] and hydroxylamines under catalyst-free and additive-free conditions has been developed, providing aryl O-aminosulfonates in good yields. Sulfonamides could also be obtained via a one-pot process through the reaction of aryldiazonium tetrafluoroborates, DABCO?(SO2)2 and amines in the presence of N-hydroxybenzotriazole. A mechanism involving the insertion of sulfur dioxide and hydrogen atom transfer is proposed and supported by theoretical calculations. (Figure presented.).
Organophosphorus and Nitro-Substituted Sulfonate Esters of 1-Hydroxy-7-azabenzotriazole as Highly Efficient Fast-Acting Peptide Coupling Reagents
Carpino, Louis A.,Xia, Jusong,Zhang, Chongwu,El-Faham, Ayman
, p. 62 - 71 (2007/10/03)
Organophosphorus esters 9, 10, 14, and 15 prepared via reaction of diethyl- and diphenylphosphoryl chloride, di(o-tolyl)phosphinyl chloride, and 2,8-dimethylphenoxaphosphinyl chloride with HOAt are excellent coupling reagents for peptide synthesis which are generally superior to their uronium/guanidinium analogues and HOBt- or HODhbt-derived phosphate ester counterparts in minimizing loss of configuration during segment coupling. The phosphinyl analogues are more shelf-stable than the phosphoryl systems. The new reagents have been tested in segment couplings leading to two tripeptides (20, 21) and a hexapeptide 22. Outstanding utility is also shown for the solid-phase assembly of the ACP decapeptide. Similar results were obtained with the 2- and 4-nitro- and 2,4-dinitrophenylsulfonyl esters derived from HOAt.