Organocatalytic Synthesis of Methylene-Bridged N-Heterobiaryls
| Autor: | David E. Stephens, Bhuwan K. Chhetri, Oleg V. Larionov, Vu T. Nguyen, Hadi D. Arman, Emily R. Clark |
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| Rok vydání: | 2016 |
| Předmět: |
Methylmagnesium chloride
Molecular Structure 010405 organic chemistry Organic Chemistry Quinoline Magnesium hydride Chemistry Techniques Synthetic Ethylenediamines Isoquinolines 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis Heterocyclic Compounds Bridged-Ring Article 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Organic chemistry Physical and Theoretical Chemistry Methylene Isoquinoline |
| Zdroj: | Organic Letters. 18:5808-5811 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A one-step synthesis of 1,1′- and 2,2′-methylene-bridged N-heterobiaryls directly from the corresponding N-heterocycles in a reaction with methylmagnesium chloride in the presence of catalytic amounts of N,N,N′N′-tetramethylethylenediamine (TMEDA) under thermal and microwave conditions is reported. The split-and-merge methylenation of 2,2′-N-heterobiaryls and the direct ortho-alkylation of quinoline and isoquinoline with Grignard reagents have also been developed. Mechanistic studies identified several intermediates and provided insights into the formation and roles of magnesium hydride species in the process. |
| Databáze: | OpenAIRE |
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