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Issue 73, 2015
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C1-Benzyl and benzoyl isoquinoline synthesis through direct oxidative cross-dehydrogenative coupling with methyl arenes

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Abstract

An oxidative cross-dehydrogenative coupling (CDC) of isoquinolines with methyl arenes has been developed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl and -benzoyl isoquinolines. The direct use of readily available methyl arenes as coupling partners avoids unproductive steps for preactivating the functional group installation, and is therefore attractive. The method exhibits excellent chemoselectivity, affording exclusive benzylated products in the presence of DTBP and a catalytic amount of Y(OTf)3, and yielding benzoylated ones with TBHP and a catalytic amount of MnO2.

Graphical abstract: C1-Benzyl and benzoyl isoquinoline synthesis through direct oxidative cross-dehydrogenative coupling with methyl arenes

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Publication details

The article was received on 10 Jun 2015, accepted on 23 Jul 2015 and first published on 23 Jul 2015


Article type: Communication
DOI: 10.1039/C5CC04791A
Citation: Chem. Commun., 2015,51, 13953-13956

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    C1-Benzyl and benzoyl isoquinoline synthesis through direct oxidative cross-dehydrogenative coupling with methyl arenes

    M. Wan, H. Lou and L. Liu, Chem. Commun., 2015, 51, 13953
    DOI: 10.1039/C5CC04791A

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