Deaminative Arylation of Amino Acid-derived Pyridinium Salts
Deaminative Arylation of Amino Acid-derived Pyridinium Salts
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DOI：
10.1021/acs.orglett.9b02643
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发表时间：
2019-09-20
期刊：
影响因子：
5.2
通讯作者：
Watson, Mary P.
中科院分区：
文献类型：
--
作者：
Hoerrner, Megan E.;Baker, Kristen M.;Watson, Mary P.
已经开发了α-吡啶鎓酯和芳基环硼氧烷的Suzuki-Miyaura交叉偶联。结合由氨基酸衍生物形成吡啶鎓盐，该方法能够使氨基酸衍生物有效地转化为α-芳基酯和酰胺。在温和的条件下，观察到对氨基酸衍生物和芳基环硼氧烷的宽官能团耐受性，包括质子官能团。机制研究支持烷基自由基中间体，类似于其他交叉耦合的烷基吡啶盐。
A Suzuki-Miyaura cross-coupling of alpha-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 alpha-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.