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Active Template Synthesis of Rotaxanes and Molecular Shuttles with Switchable Dynamics by Four-Component PdII-Promoted Michael Additions

✍ Scribed by Stephen M. Goldup; David A. Leigh; Paul J. Lusby; Roy T. McBurney; Alexandra M. Z. Slawin

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
595 KB
Volume
47
Category
Article
ISSN
0044-8249

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✦ Synopsis

Scheme 1. Synthesis of metal-coordinated [2]rotaxane [(L3)Pd] by an active template Pd II -promoted double Michael addition, and its decomplexation to hydrogen-bonded molecular shuttle H 2 L3. a) DIPEA, CH 2 Cl 2 (see Table 1 for the effects of reagent stoichiometry on the yield of rotaxane [(L3)Pd]); b) 1 m HCl (aq):CH 2 Cl 2 (1:1), reflux, 92 %. In CDCl 3 the macrocycle in H 2 L3 shuttles rapidly on the NMR timescale between the two thread ketone groups, even at 250 K; c) Pd-(OAc) 2 (2.2 equiv), CH 3 CN:CH 2 Cl 2 (1:1), 18 h, 313 K, 99 %.

📜 SIMILAR VOLUMES

Active Template Synthesis of Rotaxanes a
Active Template Synthesis of Rotaxanes and Molecular Shuttles with Switchable Dynamics by Four-Component PdII-Promoted Michael Additions
✍ Stephen M. Goldup; David A. Leigh; Paul J. Lusby; Roy T. McBurney; Alexandra M.  📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 English ⚖ 594 KB

Scheme 1. Synthesis of metal-coordinated [2]rotaxane [(L3)Pd] by an active template Pd II -promoted double Michael addition, and its decomplexation to hydrogen-bonded molecular shuttle H 2 L3. a) DIPEA, CH 2 Cl 2 (see Table 1 for the effects of reagent stoichiometry on the yield of rotaxane [(L3)Pd]