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Solid-supported copper catalysts for atom-transfer radical cyclizations: Assessment of support type and ligand structure on catalyst performance in the synthesis of nitrogen heterocycles
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UNSPECIFIED (2006) Solid-supported copper catalysts for atom-transfer radical cyclizations: Assessment of support type and ligand structure on catalyst performance in the synthesis of nitrogen heterocycles. JOURNAL OF ORGANIC CHEMISTRY, 71 (4). pp. 1471-1479. doi:10.1021/jo0521605 ISSN 0022-3263.
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Official URL: http://dx.doi.org/10.1021/jo0521605
Abstract
A range of solid supported pyridinemethanimine 9-11 and polyamine 12-15 ligands have been prepared on silica, polystyrene, and JandaJel supports. The CuCl and CuBr complexes of these supported ligands have been used to assess both the effect of the ligand type and the nature of the support upon a representative range of copper-mediated atom transfer 5-exo-trig 6, 24-25, 5-exo-dig 26, 4-exo-trig 28, and 5-endo-trig 27, 38 radical cyclizations to give nitrogen heterocycles. In addition, the effect of the nature of the support on the stereochemical outcome of the 5-exo cyclization of 25 has been probed. Generally, it was found that the type of support (e.g., polystyrene, silica, or JandaJel) had very little effect upon the efficiency and selectivity of the processes but that the nature of the ligand type immobilized was the important factor. Thus, the 5-exo cyclization of 6 and 24-26 proceeded more rapidly with the PMI ligands 9-11, whereas 4-exo cyclizations 28 and 5-endo, radical polar crossover reactions 27 and 38 proceeded more efficiently with the JJ-TEDETA ligand 15. The efficiency of the supported ligands was also compared to their solution counterparts 4 and 5. The reusability of P-PMDETA ligand system 13 was assessed in the cyclization of 6.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF ORGANIC CHEMISTRY | ||||
Publisher: | AMER CHEMICAL SOC | ||||
ISSN: | 0022-3263 | ||||
Official Date: | 17 February 2006 | ||||
Dates: |
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Volume: | 71 | ||||
Number: | 4 | ||||
Number of Pages: | 9 | ||||
Page Range: | pp. 1471-1479 | ||||
DOI: | 10.1021/jo0521605 | ||||
Publication Status: | Published |
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