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Issue 21, 2016
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Hydrohalogenative aromatization of multiynes promoted by ruthenium alkylidene complexes

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Abstract

A new functionalization method of arynes promoted by a novel catalytic role of the Grubbs-type ruthenium alkylidene complex is described. Through a sequence of aryne formation followed by their halo-functionalization, various bis-1,3-diynes were directly converted to functionalized aryl chlorides, bromides and iodides in good yields in the presence of a catalytic amount of a ruthenium alkylidene complex and halogenated hydrocarbons such as CH2Cl2, CHCl3, CH2Br2, and CH2I2. The utility of this novel transformation is demonstrated by a formal synthesis of herbindole B.

Graphical abstract: Hydrohalogenative aromatization of multiynes promoted by ruthenium alkylidene complexes

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Publication details

The article was received on 08 Mar 2016, accepted on 26 Apr 2016 and first published on 26 Apr 2016


Article type: Communication
DOI: 10.1039/C6OB00524A
Org. Biomol. Chem., 2016,14, 4782-4788

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    Hydrohalogenative aromatization of multiynes promoted by ruthenium alkylidene complexes

    R. Karmakar, K. Wang, S. Y. Yun, P. Mamidipalli and D. Lee, Org. Biomol. Chem., 2016, 14, 4782
    DOI: 10.1039/C6OB00524A

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