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Trityl tetrakis(pentafluorophenyl)borate: A sustainable precursor for multifunctional silylium Lewis acid organocatalysis
Chem Catalysis ( IF 11.5 ) Pub Date : 2024-01-04 , DOI: 10.1016/j.checat.2023.100866
Muhammad Israr , Woo Hee Kim , Dong Hyeon Kim , Han Yong Bae

In response to the growing demand for sustainable chemistry, there has been a notable surge of interest in developing efficient, metal-free, and versatile organic acid catalysts capable of facilitating the synthesis of complex valuable molecules. In this context, a silylium ion (tricoordinate, trivalent silyl cations) combined with a weakly coordinating anion as an organocatalyst could operate as a highly potent promotor in multifunctional transformations. We summarize the recent developments of silylium Lewis acid catalysis, mainly induced by trityl tetrakis(pentafluorophenyl)borate ([Ph3C]+[B(C6F5)4]) as a highly efficient catalytic precursor. The neutral, moisture-tolerant, bench-stable, metal-free salt could successfully catalyze diverse categorized transformations such as (1) hydrosilylation of alkene and alkyne, (2) reduction of carbonyl and imine, (3) carbon–fluorine bond activation, and (4) carbon–carbon bond formation. Concise mechanistic elaborations on the appeared reactions are discussed.



中文翻译:

三苯甲基四(五氟苯基)硼酸酯:多功能硅路易斯酸有机催化的可持续前体

为了满足对可持续化学不断增长的需求,人们对开发能够促进复杂的有价值分子的合成的高效、无金属和多功能有机酸催化剂的兴趣显着增加。在这种情况下,离子(三配位,三价硅基阳离子)与弱配位阴离子结合作为有机催化剂可以在多功能转化中充当高效促进剂。我们总结了硅路易斯酸催化的最新进展,主要是由三苯甲基四(五氟苯基)硼酸酯([Ph 3 C] + [B(C 6 F 5 ) 4 ])作为高效催化前体引起的。这种中性、耐湿、实验室稳定、不含金属的盐可以成功催化多种分类转化,例如(1)烯烃和炔烃的氢化硅烷化,(2)羰基和亚胺的还原,(3)碳氟键活化, (4)碳-碳键的形成。对所出现的反应进行了简明的机理阐述。

更新日期:2024-01-04
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