Copper-Catalyzed Amide Radical-Directed Cyanation of Unactivated Csp3–H Bonds
| Autor: | Peiyuan Tian, Hongwei Zhang, Cuiyu Jiang, Yulu Zhou |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Phenanthroline Organic Chemistry Regioselectivity Cyanation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Reagent Amide Functional group Physical and Theoretical Chemistry Bond cleavage |
| Zdroj: | Organic Letters. 21:1921-1925 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A method for site-selective intermolecular δ/e-Csp3-H cyanation of aliphatic sulfonamides is developed using TsCN as the cyanating reagent, catalyzed by a Cu(I)/phenanthroline complex. The mild, expeditious, and modular protocol allows efficient remote Csp3-H cyanation with good functional group tolerance and high regioselectivity. Mechanistic studies indicate that the reaction might proceed through a Cu(I)-mediated N-F bond cleavage to generate an amidyl radical, 1,5-HAT, and cyano group transfer of the resulting carbon radical with TsCN. |
| Databáze: | OpenAIRE |
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