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Issue 65, 2018
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Copper-catalyzed α-benzylation of BODIPYs via radical-triggered oxidative cross-coupling of two C–H bonds

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Abstract

An oxidative cross-dehydrogenative coupling of BODIPYs with toluene and its derivatives has been developed, allowing for the facile synthesis of a broad range of structurally diverse α-benzylated BODIPYs. The method exhibits excellent chemoselectivity, affording exclusively α-benzylated BODIPYs in the presence of t-BuOOH and a catalytic amount of Cu(OAc)2. The direct use of readily available toluene and its derivatives as coupling partners avoids unproductive steps for preactivating the functional group installation, and is therefore attractive. Most of the resulting dyes are highly emissive in the solid state due to the introduction of bulky benzyl groups onto the BODIPY core.

Graphical abstract: Copper-catalyzed α-benzylation of BODIPYs via radical-triggered oxidative cross-coupling of two C–H bonds

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Publication details

The article was received on 12 Jun 2018, accepted on 20 Jul 2018 and first published on 23 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC04679D
Citation: Chem. Commun., 2018,54, 9059-9062
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    Copper-catalyzed α-benzylation of BODIPYs via radical-triggered oxidative cross-coupling of two C–H bonds

    F. Lv, Y. Yu, E. Hao, C. Yu, H. Wang, L. Jiao and N. Boens, Chem. Commun., 2018, 54, 9059
    DOI: 10.1039/C8CC04679D

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