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Generation and reactivity of o-carborynes

机译:邻卡波因酮的产生和反应性

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摘要

o-Carboryne (1,2-dehydro-o-carborane) is a very reactive intermediate that can be generated in situ from 1-Br-2-Li-1,2-C_2B_(10)H_(10), 1-I-2-Li-1,2-C_2B_(10)H_(10) or 1-Me3Si-2-[IPh(OAc)]-1,2-C_2B_(10)H_(10). It exists in two resonance forms, a bonding form vs. a biradical form. Each form demonstrates unique reactivity patterns. o-Carboryne can undergo various types of reactions such as [4 + 2]/[2 + 2] cycloaddition, ene reaction, hydrogen abstraction, and sp~2/sp~3 C-H bond insertion reaction with a broad spectrum of substrates including alkenes, alkynes, (hetero)aromatics, ethers, and ferrocenes. It is a very useful synthon for generating a variety of functionalized carboranes that have potential applications in medicine, materials science and organometallic/coordination chemistry. This perspective offers an overview of recent advances in this interesting research field.
机译:邻-碳硼烷(1,2-脱氢-邻-碳硼烷)是一种非常活泼的中间体,可以从1-Br-2-Li-1,2-C_2B_(10)H_(10),1-I原位生成-2-Li-1,2-C_2B_(10)H_(10)或1-Me3Si-2- [IPh(OAc)]-1,2-C_2B_(10)H_(10)。它以两种共振形式存在:键合形式与双自由基形式。每种形式都展示出独特的反应模式。邻-碳硼炔可以与包括烯烃在内的多种底物进行各种类型的反应,例如[4 + 2] / [2 + 2]环加成反应,烯反应,夺氢和sp〜2 / sp〜3 CH键插入反应,炔烃,(杂)芳烃,醚和二茂铁。它是产生多种官能化碳硼烷的非常有用的合成子,在医学,材料科学和有机金属/配位化学中具有潜在应用。这种观点概述了这个有趣的研究领域的最新进展。

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