Direct Conversion of N-Alkylamines to N-Propargylamines Through C–H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules
| Autor: | Min Cao, Jessica Z. Chan, Bochao Zhang, Masayuki Wasa, Ahmet Yesilcimen, Yuyang Zhang |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Trimethylsilyl
Bioactive molecules 010402 general chemistry 01 natural sciences Biochemistry Article Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Organometallic Compounds Lewis acids and bases Amines Lewis Acids Molecular Structure Propylamines Enantioselective synthesis Late stage Stereoisomerism General Chemistry Combinatorial chemistry 0104 chemical sciences chemistry Pargyline Surface modification Catalytic method Copper |
| Zdroj: | J Am Chem Soc |
| Popis: | An efficient catalytic method to convert an α-C-H bond of N-alkylamines into an α-C-alkynyl bond was developed. In the past, such transformations were carried out under oxidative conditions, and the enantioselective variants were confined to tetrahydroisoquinoline derivatives. Here, we disclose a method for the union of N-alkylamines and trimethylsilyl alkynes, without the presence of an external oxidant and promoted through cooperative actions of two Lewis acids, B(C6F5)3 and a Cu-based complex. A variety of propargylamines can be synthesized in high diastereo- and enantioselectivity. The utility of the approach is demonstrated by the late-stage site-selective modification of bioactive amines. Kinetic investigations that shed light on various mechanistic nuances of the catalytic process are presented. |
| Databáze: | OpenAIRE |
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