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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 3.

Scope studies in [2+2] cycloadditions involving 1.

entrya alkene cycloadduct time yieldb
graphic file with name nihms391206t1.jpg graphic file with name nihms391206t2.jpg
1 Ar = 4-MePh 1 h 86%
2 Ar = 3-MePh 2.5 h 86%
3 Ar = 2-MePh 1 h 81%
4c Ar = Ph 1.5 h 79%
5d Ar = 4-FPh 2.5 h 78%
6 Ar = 4-AcOPh 3 h 78%
7d Ar = 4-(HOCH2)Ph 2.5 h 56%
8e Ar = 4-(MeO2C)Ph 4.5 h 31%
9 graphic file with name nihms391206t3.jpg graphic file with name nihms391206t4.jpg 2 h 87%f
10d graphic file with name nihms391206t5.jpg graphic file with name nihms391206t6.jpg 3.5 h 0%
11 graphic file with name nihms391206t7.jpg graphic file with name nihms391206t8.jpg 3.5 h 67%
12d graphic file with name nihms391206t9.jpg graphic file with name nihms391206t10.jpg 2.5 h 48%g
13 graphic file with name nihms391206t11.jpg graphic file with name nihms391206t12.jpg 4.5 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. Products isolated in >10:1 d.r. unless otherwise noted.

c

Alkene 1 added over 1 h.

d

Alkene 1 added over 2 h.

e

Alkene 1 added over 4 h.

f

9:1 d.r.

g

3:1 d.r.