Metal- and additive-free photoinduced borylation of haloarenes.
Metal- and additive-free photoinduced borylation of haloarenes.
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DOI：
10.1038/nprot.2016.184
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发表时间：
2017-03
期刊：
影响因子：
14.8
通讯作者：
Larionov OV
中科院分区：
文献类型：
--
作者：
Mfuh AM;Schneider BD;Cruces W;Larionov OV
硼酸和硼酸酯在合成有机化学、分子传感器、材料科学、药物发现和催化等领域具有重要作用。硼酸和硼酸酯的许多当前应用需要具有非常低水平的过渡金属污染的材料。然而，目前用于合成硼酸的大多数方法需要过渡金属催化剂和配体，其必须通过另外的纯化程序除去。该方案描述了一种简单的、不含金属和添加剂的卤代芳烃直接转化为硼酸和硼酸酯的方法。这种光诱导的硼基化方案不需要昂贵和有毒的金属催化剂和配体，并产生无害和易于去除的副产物。此外，该反应可以在普通级溶剂中以多克规模进行，而不需要将反应混合物脱氧。设置和纯化步骤通常在1-3小时内完成。反应可以过夜进行，并且该方案可以在13-16小时内完成。本方案中描述的两个代表性程序提供了制备硼酸（3-氰基苯基硼酸）和硼酸酯（1，1-苯二硼酸双（频哪醇）酯）的详细信息。我们还讨论了该方法的其他细节，这将有助于在其他卤代芳烃底物的协议的应用。
Boronic acids and esters have crucial roles in the areas of synthetic organic chemistry, molecular sensors, materials science, drug discovery, and catalysis. Many of the current applications of boronic acids and esters require materials with very low levels of transition metal contamination. Most of the current methods for the synthesis of boronic acids require, however, transition metal catalysts and ligands that have to be removed via additional purification procedures. This protocol describes a simple, metal- and additive-free method of conversion of haloarenes directly to boronic acids and esters. This photoinduced borylation protocol does not require expensive and toxic metal catalysts and ligands and produces innocuous and easy-to-remove by-products. Furthermore, the reaction can be carried out on multigram scales in common grade solvents without the need for reaction mixtures to be deoxygenated. The setup and purification steps are typically accomplished within 1–3 h. The reactions can be run overnight, and the protocol can be completed within 13–16 h. Two representative procedures that are described in this protocol provide details for preparation of a boronic acid (3-cyanopheylboronic acid) and a boronic ester (1,-benzenediboronic acid bis(pinacol)ester). We also discuss additional details of the method that will be helpful in the application of the protocol to other haloarene substrates.
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DOI：
10.1007/978-3-319-13054-5_10
发表时间：
2015-01-01
期刊：
SYNTHESIS AND APPLICATION OF ORGANOBORON COMPOUNDS
影响因子：
--
作者：
Jaekle, Frieder
通讯作者：
Jaekle, Frieder
影响因子：
15
作者：
Mfuh AM;Nguyen VT;Chhetri B;Burch JE;Doyle JD;Nesterov VN;Arman HD;Larionov OV
通讯作者：
Larionov OV
影响因子：
3.6
作者：
Mella, M;Coppo, P;Albini, A
通讯作者：
Albini, A
间歇和连续流动条件下芳基卤化物的高效无金属光化学硼基化
影响因子：
8.4
作者：
Chen K;Zhang S;He P;Li P
通讯作者：
Li P
影响因子：
3.8
作者：
Li, Gang;Schoneker, Dave;Kauffman, John F.
通讯作者：
Kauffman, John F.