School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.
Org Lett. 2018 Oct 5;20(19):6144-6147. doi: 10.1021/acs.orglett.8b02615. Epub 2018 Sep 17.
An enantiospecific coupling between alkylboronic esters and lithiated aryl hydrazines is described. The reaction proceeds under transition-metal-free conditions and is promoted by acylation of a hydrazinyl arylboronate complex, which triggers a N-N bond cleavage with concomitant 1,2-metalate rearrangement. Judicious choice of the acylating agent enabled the synthesis of ortho- and para-substituted anilines with essentially complete enantiospecificity from a wide range of boronic ester substrates.
本文描述了手性烷基硼酸酯与连位芳基腙锂之间的对映选择性偶联反应。该反应在无过渡金属条件下进行，酰化芳基硼酸肼配合物可促进反应的进行，同时引发 N-N 键断裂和 1,2-金属迁移重排。通过合理选择酰化剂，可从广泛的硼酸酯底物中基本实现对映选择性合成邻位和对位取代苯胺。
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