[2]Rotaxanes through palladium active-template oxidative heck cross-couplings

Journal of the American Chemical Society

Volumn 129, Issue 40, 2007, Pages 12092-12093

  Crowley, James D ^a   Hänni, Kevin D ^a   Lee, Ai Lan ^a   Leigh, David A ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BORONIC ACID DERIVATIVE; PALLADIUM; ROTAXANE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HECK REACTION; MACROMOLECULE; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 35048903031     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075219t     Document Type: Article

References (22)

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14. For stoichiometric active-metal template Ullman and Glaser coupling rotaxane syntheses, in which the metal does not turnover, see: Saito, S.; Takahashi, E.; Nakazono, K. Org. Lett. 2006, 8, 5133-5136.
15. An outline of these macrocycle-Pd(O) investigations is given in the Supporting Information. Pd(0)-catalyzed Suzuki reactions have been used as the stoppering reaction in the synthesis of cyclodextrin rotaxanes; see: (a) Terao, J.; Tang, A.; Michels, J. J.; Krivokapic, A.; Anderson, H. L. Chem. Commun. 2004, 56-57.
16. (b) Klotz, E. J. F.; Claridge, T. D. W.; Anderson, H. L. J. Am. Chem. Soc. 2006, 128, 15374-15375.
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18. 2f-h suggest that bidentate N ligands such as bipyridine and phenanthroline are the most effective at promoting oxidative Heck reactions at room temperature. Carrying out the reaction in Table 1, entry 1, with a monodentate pyridine macrocycle resulted in no rotaxane formation and only 10% conversion to the thread.
19. 2 as the sole oxidant produced only 26% rotaxane (other reagents and conditions as per Table 1, entry 1). See Supporting Information for further details.
20. 2 was found to be the optimal solvent system for the studies presented here. See Supporting Information for further details.
21. 2h This difference is probably due to steric effects.
22. Unoptimized yield. Rotaxane 16 proved difficult to isolate free from the accompanying byproduct thread.