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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 …
Hydroalkynylation Of Oxocarbenium Intermediates Via Au(I) Catalysis, Courtney Smith Smith
Hydroalkynylation Of Oxocarbenium Intermediates Via Au(I) Catalysis, Courtney Smith Smith
USF Tampa Graduate Theses and Dissertations
Au(I) catalysis has recently emerged as a powerful tool for the realization of a broad range of organic transformations. Despite this rapid development, attaining selectivity and maintaining catalyst stability remain significant challenges. Rational ligand design, such as the employment of NHC or TA ligands, has been used to confront these issues. This thesis focuses on the use of Au(I) catalysts bearing these ligands for the selective hydroalkynylation of enol ethers. By employing a TA-Au stabilized catalyst, [(OAr)3PAu(TA-H)]OTf, the intermolecular hydroalkynylation of enol ethers, a substrate that is well-known to promote decomposition of the gold cation, was efficiently achieved. …