通过烯基硼酸酯的区域选择性 Wacker 氧化反应合成 α-硼代酮。
Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates.
机构信息
Davenport Research Laboratories, Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , ON M5S 3H6 , Canada.
Department of Chemistry , Brock University , 1812 Sir Isaac Brock Way , St. Catherines , ON L2S 3A1 , Canada.
出版信息
Org Lett. 2018 Sep 7;20(17):5300-5303. doi: 10.1021/acs.orglett.8b02234. Epub 2018 Aug 21.
As part of a program aimed at metal-catalyzed oxidative transformations of molecules with carbon-metalloid bonds, the synthesis of α-borylated ketones is reported via regioselective TBHP-mediated Wacker-type oxidation of N-methyliminodiacetic acid (MIDA)-protected alkenylboronates. The observed regioselectivity correlates with the hemilabile nature of the B-N dative bond in the MIDA boronate functional group, which allows boron to guide selectivity through a neighboring group effect.
作为旨在实现碳-类金属键分子的金属催化氧化转化的项目的一部分，本文报道了通过 N-甲基亚氨基二乙酸（MIDA）保护的烯基硼酸酯的 TBHP 介导的 Wacker 型氧化反应，实现了α-硼化酮的区域选择性合成。观察到的区域选择性与 MIDA 硼酸酯官能团中 B-N 配位键的半配位性质相关，该性质允许硼通过邻基效应引导选择性。
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