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Issue 13, 2014
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Generation and reactivity of o-carborynes

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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-C2B10H10, 1-I-2-Li-1,2-C2B10H10 or 1-Me3Si-2-[IPh(OAc)]-1,2-C2B10H10. 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 sp2/sp3 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.

Graphical abstract: Generation and reactivity of o-carborynes

  • This article is part of the themed collection: Carboranes
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Publication details

The article was received on 30 Sep 2013, accepted on 30 Oct 2013 and first published on 15 Nov 2013

Article type: Perspective
DOI: 10.1039/C3DT52711E
Citation: Dalton Trans., 2014,43, 4925-4934
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    Generation and reactivity of o-carborynes

    Z. Qiu and Z. Xie, Dalton Trans., 2014, 43, 4925
    DOI: 10.1039/C3DT52711E

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