Reaction of secondary and tertiary aliphatic halides with aromatic aldehydes mediated by chromium(II): a selective cross-coupling of alkyl and ketyl radicals |
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| Authors: | Ludger A Wessjohann Gisela Schmidt |
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| Institution: | a Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany
b Laboratory of Technological Processes and Catalysis, Institute of Chemistry, Universidade Federal do Rio Grande do Sul, Bento Gonçalves 9500, Porto Alegre-RS, CEP: 91501-970, PO Box 15003, Brazil |
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| Abstract: | Takai-Utimoto reactions with secondary and tertiary aliphatic halides usually failed according to previous reports. Now, significant improvements could be achieved, and especially secondary aliphatic halides can be coupled to aromatic aldehydes in yields of up to >95%. A variety of processes are competing with the desired one, and thus conditions must be adapted to the nature of the aldehyde as well as the aliphatic halide used, as the outcome of these reactions is strongly affected by the putative radical intermediates. |
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| Keywords: | Organometallic catalysis Chromium alkyls&mdash secondary and tertiary Catalysis&mdash cobalt Radical intermediates Salt effect&mdash lithium iodide Barbier reaction&mdash Grignard-type reaction |
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