硼酸催化唑类化合物的区域选择性-α-烷基化反应。
Borinic Acid Catalyzed Regioselective -Alkylation of Azoles.
机构信息
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
出版信息
J Org Chem. 2022 Apr 15;87(8):5385-5394. doi: 10.1021/acs.joc.2c00281. Epub 2022 Apr 6.
A method for regioselective -alkylation of ambident, azole-type heterocycles with alkene or epoxide electrophiles is described. In the presence of diphenylborinic acid (PhBOH) and an amine cocatalyst, heterocyclic nucleophiles such as 1,2,3- and 1,2,4-triazoles, substituted tetrazoles, and purine are activated toward selective -functionalization. The scope of electrophilic partners includes enones, 2-vinylpyridine, phenyl vinyl sulfone, a dehydroalanine derivative, and epoxides. Mechanistic studies, including in situ B NMR spectroscopy and kinetic analysis, are discussed.
一种区域选择性 -烷基化的 ambident，azole 型杂环与烯烃或环氧化物亲电试剂的方法被描述。在二苯基硼酸（PhBOH）和胺助催化剂的存在下，杂环亲核试剂如 1,2,3-和 1,2,4-三唑、取代的四唑和嘌呤被激活，以实现选择性 -功能化。亲电试剂的范围包括烯酮、2-乙烯吡啶、苯乙烯砜、脱氢丙氨酸衍生物和环氧化物。讨论了包括原位 B NMR 光谱和动力学分析在内的机理研究。
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