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. Author manuscript; available in PMC: 2012 Sep 7.
Published in final edited form as: J Am Chem Soc. 2011 Aug 16;133(35):13984–14001. doi: 10.1021/ja203733q

Table 2.

Effect of alkyne on the Cu(OAc)2-accelerated reactions involving chelating azides 1–3.a

Entry graphic file with name nihms317363t2.jpg Timeb Timeb Timeb
graphic file with name nihms317363t3.jpg graphic file with name nihms317363t4.jpg graphic file with name nihms317363t5.jpg
1 graphic file with name nihms317363t6.jpg < 5 min < 5 min 8 h (84%)c
2 graphic file with name nihms317363t7.jpg < 5 min 5–6 min 2.5 h
3 graphic file with name nihms317363t8.jpg < 5 min < 5 min 8 h
4 graphic file with name nihms317363t9.jpg < 5 min < 5 min 30 min
5 graphic file with name nihms317363t10.jpg < 5 min 8 h (93%)c 8 h (75%)c
6 graphic file with name nihms317363t11.jpg 2.5 h 25 min 8 h (94%)c
7 graphic file with name nihms317363t12.jpg 8 h (84%)c 8 h (96%)c 2 h
a

Reaction conditions: azide (0.2 mmol), alkyne (0.22 mmol), Cu(OAc)2 (5 mol%), in CH3OH (0.5 mL), rt. For reactions involving azide 3, TEA (0.2 mmol) was included.

b

Time for azide to disappear on TLC, followed by the confirmation of a full conversion (> 95%) by 1H NMR.

c

Incomplete conversion with percentage yield in parenthesis.