Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts
Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts
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DOI：
10.1021/acs.oprd.8b00248
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发表时间：
2018-11-01
影响因子：
3.4
通讯作者：
Fontaine, Frederic-Georges
中科院分区：
文献类型：
--
作者：
Jayaraman, Arumugam;Castro, Luis C. Misal;Fontaine, Frederic-Georges
提出了一种实用、可扩展的杂芳烃硼化和硼化脱芳的无金属催化方法。该合成方法采用1-NHR2-2-BF3-C6H4形式的廉价且易于合成的台架稳定预催化剂，商业上和合成上可获得的杂芳烃为底物，蒎烷硼烷为硼化试剂。在无溶剂条件下，不使用Schlenk技术或手套箱，在2和50 g尺度上制备了几种硼化杂环。使用这种具有成本效益的绿色方法还实现了一种杂二烯底物的千克级硼化，这表明我们的方法可以方便地在精细化工行业中实施。
A practical and scalable metal-free catalytic method for the borylation and borylative dearomatization of heteroarenes has been developed. This synthetic method uses inexpensive and conveniently synthesizable bench-stable precatalysts of the form 1-NHR2-2-BF3-C6H4, commercially and synthetically accessible heteroarenes as substrates, and pinacolborane as the borylation reagent. The preparation of several borylated heterocycles on 2 and 50 g scales was achieved under solvent-free conditions without the use of Schlenk techniques or a glovebox. A kilogram-scale borylation of one of the heteroarene substrates was also achieved using this cost-effective green methodology to exemplify the fact that our methodology can be conveniently implemented in fine chemical industries.