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Regioselective Insertion of Carborynes into Ethereal C−H Bond: Facile Synthesis of α-Carboranylated Ethers

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posted on 20.04.2011, 00:00 by Sunewang R. Wang, Zaozao Qiu, Zuowei Xie
Carborynes can exist in two resonance forms, bonding form vs biradical form. The biradical form can be readily generated via the elimination of LiI from 1-iodo-n-lithio-1,n-C2B10H10 (n = 2, 7) under UV irradiation. They can undergo α-C−H bond insertion with aliphatic ethers, affording α-carboranylated ethers in excellent regioselectivity at room temperature. This serves as a new methodology for the generation of a series of functionalized carboranes bearing alkoxy units.