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Issue 33, 2015
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Manganese catalyzed C–H functionalization of indoles with alkynes to synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is the key to control selectivity

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Abstract

The Mn-catalyzed C–H alkenylation reactions of indole with terminal- and internal-alkynes have been developed. In the presence of a catalytic amount of acid, the procedure efficiently affords bis/trisubstituted indolyl-alkenes in a highly regio- and stereo-selective manner. Without the addition of acid, the reaction undergoes a [2+2+2] cyclization process to give carbazoles with release of hydrogen gas. Notably, the directing pyrimidyl group can be readily removed. Experimental studies reveal that the reaction is initiated by a C–H activation step and the acid is the selectivity controller via a hydrogen transfer process.

Graphical abstract: Manganese catalyzed C–H functionalization of indoles with alkynes to synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is the key to control selectivity

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Publication details

The article was received on 11 Jan 2015, accepted on 15 Mar 2015 and first published on 16 Mar 2015


Article type: Communication
DOI: 10.1039/C5CC00249D
Citation: Chem. Commun., 2015,51, 7136-7139

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    Manganese catalyzed C–H functionalization of indoles with alkynes to synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is the key to control selectivity

    L. Shi, X. Zhong, H. She, Z. Lei and F. Li, Chem. Commun., 2015, 51, 7136
    DOI: 10.1039/C5CC00249D

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