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. Author manuscript; available in PMC: 2010 Dec 1.
Published in final edited form as: Org Lett. 2010 Sep 3;12(17):3780–3783. doi: 10.1021/ol101418d

Table 1.

A Cu(II)-Catalyzed Ynamide-[2 + 2] Cycloaddition.

graphic file with name nihms241177u2.jpg
entry R = solvent catalyst [mol %] temp [°C] time [h]a yield [%]b
1 10: H CH3CN In(OTf)2 [30] - 15 1 --c
2 10: H CH3CN Sc(OTf)3 [30] - 15 1 --c
3 10: H CH3CN Cu(OTf)2 [10] 25 – 80 4 --d
4 10: H CH3CN AgSbF6 [10] 0 – 80 5 --d
5 10: H CH3CN AgSbF6 [10] 50 – 120 2 --d
6 10: H CH2Cl2 CuCl2/AgSbF6 [20/42] - 78 – 25 10 ≤ 5d,e
7 12: Me CH2Cl2 CuCl2/AgSbF6 [20/60] - 40 1 72
8 12: Me CH2Cl2 CuCl2/AgSbF6 [20/60] - 15 1 77
9 12: Me CH2Cl2 CuCl2/AgSbF6 [20/60] 0 1 76
a

Time for syringe pump addition of a solution of 10 [or 12] and enone.

b

Isolated yields.

c

Hydrolysis of 10 was the major outcome.

d

No reaction – recovered starting material 10.

e

Polymerization was the major outcome in addition to hydrolysis.