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Transition-Metal-Free Homocoupling of Organomagnesium Compounds

Authors

  • Arkady Krasovskiy Dr.,

    1. Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-21-80-776-80
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  • Alexander Tishkov Dr.,

    1. Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-21-80-776-80
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  • Vicente del Amo Dr.,

    1. Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-21-80-776-80
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  • Herbert Mayr Prof. Dr.,

    1. Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-21-80-776-80
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  • Paul Knochel Prof. Dr.

    1. Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-21-80-776-80
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  • We thank the Fonds der Chemischen Industrie and Merck Research Laboratories (MSD) for financial support. We also thank V. Malakhov for the performance of some preliminary experiments as well as Chemetall GmbH (Frankfurt) and BASF AG (Ludwigshafen) for the generous gift of chemicals. V. del Amo thanks the Alexander von Humboldt Foundation for financial support.

Abstract

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Without palladium or copper: A wide range of functionalized Grignard compounds were coupled by using diphenoquinone 1 as an electron acceptor. The oxidative dimerization of alkenylmagnesium reagents proceeds with complete retention of the stereochemistry (see scheme; TBDMS=tert-butyldimethylsilyl).

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