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Recent Advance in Transition Metal-Catalyzed Carboxylic Acid Guided B−H Functionalization of Carboranes
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2022-11-30 , DOI: 10.1002/adsc.202201183
Qian Wang, Bifu Liu, Kejun Feng, A. Stephen K. Hashmi

Carboranes, a three-dimensional class of carbon-boron molecular clusters with remarkable electronic, physical, chemical characteristics, have proved as useful building blocks in boron neutron capture therapy agents, supramolecular design, optoelectronics, nanomaterials and organometallic/coordination chemistry. Thus, various organic modifications of the B−H and C−H functionalities in carboranes have been developed. These methods with great success utilize directing groups, such as carboxylic acids, to achieve a selective B−H functionalization of carboranes. The carboxyl group can be easily introduced to carboranes and then be removed after reactions. On the other hand, assisted by the carboxyl group a highly regioselective electrophilic attack at the electron-rich positions B(4) and B(5) of the cage generates five-membered metallacyclic intermediates, which then undergo further transformation. In this review, we show that transition metal-catalyzed decarboxylation cross coupling reactions offer an opportunity for the selective and direct B−H activation of carboranes.

中文翻译:

过渡金属催化羧酸引导碳硼烷B−H官能化的最新进展

碳硼烷是一种三维类碳硼分子簇,具有显着的电子、物理和化学特性,已被证明是硼中子俘获治疗剂、超分子设计、光电子学、纳米材料和有机金属/配位化学中有用的组成部分。因此,已经开发了碳硼烷中 B−H 和 C−H 官能团的各种有机修饰。这些方法非常成功地利用定向基团(例如羧酸)来实现碳硼烷的选择性 B−H 官能化。羧基可以很容易地引入碳硼烷,然后在反应后被去除。另一方面,在羧基的协助下,对笼的富电子位置 B(4) 和 B(5) 进行高度区域选择性亲电攻击,生成五元金属环中间体,然后进行进一步转化。在这篇综述中,我们表明过渡金属催化的脱羧交叉偶联反应为碳硼烷的选择性和直接 B−H 活化提供了机会。
更新日期:2022-11-30
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