Deaminative Arylation of Amino Acid-derived Pyridinium Salts
| Autor: | Corey H. Basch, Mary P. Watson, Earl M. Bampo, Megan E. Hoerrner, Kristen M. Baker |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Boron Compounds
chemistry.chemical_classification Molecular Structure Pyridines 010405 organic chemistry Organic Chemistry Esters 010402 general chemistry Amides 01 natural sciences Biochemistry Article 0104 chemical sciences Amino acid chemistry.chemical_compound chemistry Deamination Organic chemistry Salts Pyridinium Amino Acids Physical and Theoretical Chemistry |
| Zdroj: | Org Lett |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A Suzuki–Miyaura cross-coupling of α-pyridinium esters and arylboroxines has been developed. Combined with formation of the pyridinium salts from amino acid derivatives, this method enables amino acid derivatives to be efficiently transformed into α-aryl esters and amides. Under the mild conditions, broad functional group tolerance on both the amino acid derivatives and the arylboroxine are observed, including protic functional groups. Mechanistic studies support an alkyl radical intermediate, similar to other cross-couplings of alkylpyridinium salts. |
| Databáze: | OpenAIRE |
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