Copper-Mediated sp 2 C–H Chlorination with Trichloroacetamide Using a Removable Directing Group
| Autor: | Jie Jack Li, Arya Tehrani, Wan-Chen Cindy Lee |
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| Rok vydání: | 2017 |
| Předmět: |
Denticity
Organic base 010405 organic chemistry Ammonium nitrate Organic Chemistry Copper mediated chemistry.chemical_element 010402 general chemistry 01 natural sciences Copper Catalysis 0104 chemical sciences chemistry.chemical_compound Cerium chemistry Group (periodic table) Polymer chemistry Chlorine Organic chemistry |
| Zdroj: | Synthesis. 49:2865-2872 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0036-1590503 |
| Popis: | 2-Aminophenyl-1H-pyrazole was discovered as a removable, bidentate directing group for copper-mediated aerobic oxidative sp 2 C–H bond chlorination employing trichloroacetamide as a new chlorine source. 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 mono- and dichlorinated products in moderate to excellent yields. This directing group can be removed oxidatively with cerium ammonium nitrate (CAN). |
| Databáze: | OpenAIRE |
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