Organotrifluoroborates: Another Branch of the Mighty Oak
Organotrifluoroborates: Another Branch of the Mighty Oak
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DOI：
10.1021/acs.joc.5b00981
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发表时间：
2015-08-21
影响因子：
3.6
通讯作者：
Molander, Gary A.
中科院分区：
文献类型：
--
作者：
Molander, Gary A.
在过去的二十年里，有机三氟硼酸盐已经从化学珍品发展成为有机分子制备的重要试剂。除了它们通常独特的反应模式之外，这些试剂的有利特征包括它们易于制备/分离、可靠的结晶度、增强的稳定性和单体结构。目前，有超过600种结构多样的此类试剂可商购获得，并且作者的实验室已报道了超过850种此类化合物。有机三氟硼酸盐可通过简单的官能团转化用作各种最终产物的贮存稳定的前体，并且还已被用作文库或单独形式的芳族、烯基、炔基和烷基底物之间的交叉偶联反应中的伴侣。在交叉偶联反应的领域内，有机三氟硼酸盐提供了一个实际的入口，使用其他有机金属试剂不容易访问的子结构实体，最近，交叉偶联的一种新的机制范式的发展有望扩大范围可访问的交叉偶联合作伙伴，甚至进一步包括单电子和双电子过程。
Over the past two decades, organotrifluoroborates have evolved from being chemical curiosities to important reagents for the elaboration of organic molecules. Aside from their often-unique reactivity patterns, favorable features of these reagents include their ease of preparation/isolation, reliable crystallinity, enhanced stability, and monomeric structure. Currently >600 structurally diverse reagents of this class are commercially available, and >850 such compounds have been reported from the author's laboratory. The organotrifluoroborates can be utilized as shelf-stable precursors to a variety of end products through simple functional group transformations and have also been employed as partners in cross-coupling reactions between aromatic, alkenyl, alkynyl, and alkyl substrates in library or individual formats. Within the realm of cross-coupling reactions, organotrifluoroborates provide a practical entry to substructural entities not readily accessed using other organometallic reagents, and most recently, the development of a novel mechanistic paradigm for cross-coupling promises to expand the range of accessible cross-coupling partners even further to include both single- and two-electron processes.