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. Author manuscript; available in PMC: 2013 Jun 25.
Published in final edited form as: Chem Sci. 2012 Jun 25;3(9):2807–2811. doi: 10.1039/C2SC20658G

Table 4.

Scope studies of crossed cycloadditions involving 7a.

entrya substrate cycloadduct time yieldb
graphic file with name nihms391206t13.jpg graphic file with name nihms391206t14.jpg
1 R1 = OTBS 2.5 h 63%
2 R1 = OAc 4 h 91%
3 R1 = Cl 3 h 37%
4 R1 = OH 3 h 74%
5 R1 = NHTs 24 h 74%
6 graphic file with name nihms391206t15.jpg graphic file with name nihms391206t16.jpg 1.5 h 79%
7 graphic file with name nihms391206t17.jpg graphic file with name nihms391206t18.jpg 1.5 h 59%
8 graphic file with name nihms391206t19.jpg graphic file with name nihms391206t20.jpg 24 h 28%
9 graphic file with name nihms391206t21.jpg
graphic file with name nihms391206t23.jpg
graphic file with name nihms391206t22.jpg
graphic file with name nihms391206t24.jpg
24 h 0%
10 R2 = TBSO 2.5 h 88%
11 R2 = BnO 1.5 h 79%
12 R2 = AcO 24 h 0%
a

Reactions were irradiated with a 20 W compact fluorescent lightbulb at −15 °C using 0.25 mol% Ru(bpm)3(BArF)2, 1 equiv of 1, and 2 equiv of coupling partner.

b

Values reflect the average isolated yields from two reproducible experiments.