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C(Sp2)–H Functionalizations Employing 2-Aminophenyl-1h-Pyrazole As A New Removable Directing Group, Wan-Chen Lee
C(Sp2)–H Functionalizations Employing 2-Aminophenyl-1h-Pyrazole As A New Removable Directing Group, Wan-Chen Lee
Master's Theses
2-Aminophenyl-1H-pyrazole (2-APP) was discovered as a novel removable bidentate directing group for copper-mediated aerobic oxidative C(sp2)–H bond amidation and sulfonamidation bearing a wide range of sulfonamides, When Cu(OAc)2 was employed as the copper source, 1,1,3,3-tetramethylguanidine (TMG) as an organic base, the reaction, optimally carried out overnight in DMSO at 80 °C in open air, produced a variety of products in moderate to excellent yields. In addition, C(sp2)–H bond chlorination has been developed by using this auxiliary, employing trichloroacetamide as a new chlorine source. Furthermore, this unprecedented directing group also can assist copper-mediated regio-selective hydroxylation, and ortho-alkynylation/annulation by using Cu(OAc)2 as …