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Gold-Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes

Authors

  • A. Stephen K. Hashmi,

    Corresponding author
    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
    • Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
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  • Marcel Wieteck,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
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  • Ingo Braun,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
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  • Pascal Nösel,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
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  • Linda Jongbloed,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
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  • Matthias Rudolph,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
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  • Frank Rominger

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-6221-54-4205, (http://www.hashmi.de)
    2. Crystallographic investigation
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Abstract

A series of easily accessible arene-1,2-diynes, bearing one aryl substituent on one of the alkynyl groups, is readily converted to dibenzopentalenes in good yields by gold(I) catalysts. The participation of gold acetylides could be proven by the direct conversion to the corresponding gem-diaurated dibenzopentalenes with a gold catalyst. From an experiment with a gold acetylide complex and stoichiometric amounts of the gold “catalyst” the corresponding gem-diaurated complex of a dibenzopentalene could be obtained and characterized by X-ray crystal structure analysis. Labelling studies with deuterated alkynes show the expected deuteration of the two remaining positions of the pentalene core. All this provides evidence for a dual activation mode of the reaction and gold(I) vinylidene complexes as intermediates of the catalytic cycle.

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