Fig. 2
From: An isolable catenane consisting of two Möbius conjugated nanohoops
Synthetic routes to catenane 1. The reaction conditions were as follows: (i) 2 (1 equiv), 3 (2.5 equiv), Pd(PPh3)4 (10 mol%), Na2CO3 (20 equiv), and toluene/water, 100 oC, 24 h. (ii) 4 (1 equiv), B2pin2 (4 equiv), Pd(OAc)2 (10 mol%), S-Phos (20 mol%), K3PO4 (6 equiv), and 1,4-dioxane, 85 oC, 24 h. (iii) 5 (1 equiv), Cu(CH3CN)4PF6 (0.5 equiv), and THF, 25 oC, 10 min. (iv) Crude 6 in solution, Pd(PPh3)2Cl2 (1 equiv), KF (20 equiv), and THF/H2O, 25 oC, 24 h. (v) Crude product 7, TMSCN (10 equiv), KF (15 equiv), and CH2Cl2/CH3CN/H2O, 25 oC, 6 h. (vi) 8 (1 equiv), THF, and freshly prepared sodium naphthalenide (0.2 M solution in THF, 15 equiv), –78 oC, 1.5 h. Bpin boronic acid pinacol ester, Me methyl, Ph phenyl, Cy cyclohexyl, TMS trimethylsilyl, OAc acetate, THF tetrahydrofuran
