Tetrahedron Letters ( IF 1.5 ) Pub Date : 2017-09-11 , DOI: 10.1016/j.tetlet.2017.09.019 Irena S. Akhrem , Dzhul'etta V. Avetisyan , Lyudmila V. Afanas'eva , Oleg I. Artyushin , Nikolai D. Kagramanov , Andrey L. Sigan
The one-pot, regioselective synthesis of branched diacid derivatives – diesters, dithioesters, diamides [YC(O)O(CH2)mC(Me)2OC(O)Y] and diketones of aromatic and heteroaromatic series, [ArCO(CH2)mC(Me)2C(O)Ar,) from available linear acyl halides, CnH2 n+1COCl (n = 7–9), CO (1 at) and various nucleophiles (YH = EtOH, CF3CH2OH, H(CF2)2CH2OH, thiophene, anisole, Et2NH, aniline, and morpholine) in the presence of the superelectrophilic complex, CBr4·2AlBr3 has been performed for the first time. This method provides access to new and promising groups of dicarboxylic acid derivatives and diketones containing quaternary carbon atom and remote functional groups.
中文翻译:
从线性酰基卤一锅合成含季碳原子和远端官能团的二羧酸衍生物和二酮的新方法
一锅的区域选择性合成支链二酸衍生物–二酯,二硫酯,二酰胺[YC(O)O(CH 2)m C(Me)2 OC(O)Y]以及芳族和杂芳族系列的二酮[ArCO( CH 2)m C(Me)2 C(O)Ar,)来自可用的线性酰基卤,C n H 2 n + 1 COCl(n = 7–9),CO(1 at)和各种亲核试剂(YH = EtOH ,CF 3 CH 2 OH,H(CF 2)2 CH 2 OH,噻吩,苯甲醚,Et 2 NH,苯胺和吗啉)在超亲电子配合物CBr 4的存在下·2AlBr 3首次进行。该方法提供了获得新的和有希望的二元羧酸衍生物和含有季碳原子和远端官能团的二酮基的途径。