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Synthesis 2015; 47(02): 279-288
DOI: 10.1055/s-0034-1378673
DOI: 10.1055/s-0034-1378673
paper
Exploiting Palladium-Catalyzed Cross-Coupling for the Synthesis of 2-Aryl-Substituted 1-Aminocyclopropylphosphonates
Further Information
Publication History
Received: 06 August 2014
Accepted after revision: 07 September 2014
Publication Date:
15 October 2014 (online)
Abstract
A series of 2-aryl-substituted 1-aminocyclopropylphosphonates containing an additional remote phosphonate group have been synthesized starting from readily accessible dimethyl (1R*,2R*)-2-(4-bromophenyl)-1-formamidocyclopropylphosphonate using cross-coupling methodology. Different types of palladium-catalyzed reactions for carbon–carbon and carbon–phosphorus bond formation were realized. In each case the optimum conditions were found to obtain the desired products in high yield in both small- and large-scale experiments.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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We have chosen Pd(dba)2 rather than the most commonly used Pd(OAc)2 to simplify the arrangement of the catalytic cycle avoiding the pre-stage of Pd(II) reduction and the problem of the following competitive oxidative addition with aryl halide (with starting of the catalytic cycle) or with H-phosphonate (with formation of catalytically inactive Pd(II) species):
The NMR spectra of the formamide compounds 1, 4, 6, 8, 9, 13, 14 reveal two sets of signals corresponding to a pair of rotamers arising from the resonance stabilization within formamide moiety. For details see:
Other examples of diethyl vinylphosphonate in the Mizoroki–Heck reaction:
For beneficial effects of tri-o-tolylphosphine see: