Selective mono- and 1,2-difunctionalisation of cyclopentene derivatives via Mg and Cu intermediates |
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| Authors: | Despotopoulou Christina Bauer Richard C Krasovskiy Arkady Mayer Peter Stryker Jeffrey M Knochel Paul |
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| Institution: | 1. Department Chemie und Biochemie, Ludwig‐Maximilians‐Universit?t München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49)?89‐2180‐77680;2. Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada |
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| Abstract: | A single Br/Mg exchange of 1,2-dibromocyclopentene with iPrMgCl LiCl provides the corresponding beta-bromocyclopentenylmagnesium reagent, which can then be reacted with various electrophiles (yields: 65-82 %). In the presence of a secondary alkylmagnesium halide and Li2CuCl4 (2 mol %), these 2-bromoalkenylmagnesium compounds undergo bromine substitution and can then further react with electrophiles to give 1,2-difunctionalised cyclopentenes (63-79 %). The mechanism of this process is discussed. |
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| Keywords: | alkenylmagnesium reagents cross‐coupling Cu catalysis functionalized cyclopentenes Grignard reaction |
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