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. Author manuscript; available in PMC: 2010 Oct 21.
Published in final edited form as: J Am Chem Soc. 2009 Oct 21;131(41):14604–14605. doi: 10.1021/ja903732v

Table 1.

Effect of aryl enone structure in photocatalytic crossed cycloadditions with methyl vinyl ketone 2a

entry enone cycloadduct yieldb d.r.b
graphic file with name nihms121383t1.jpg graphic file with name nihms121383t2.jpg
1 R1 = Ph 84% >10:1
2 R1 = 4-ClPh 82% >10:1
3 R1 = 4-MeOPh 53% >10:1
4 R1 = 2-furyl 74% >10:1
5 R1 = Et 0% --
graphic file with name nihms121383t3.jpg graphic file with name nihms121383t4.jpg
6 R2 = Et 70% 6:1
7c R2 = i-Pr 64% >10:1
8d R2 = t-Bu 8% >10:1
9 R2 = CH2OBn 61% >10:1
a

Unless otherwise noted, reactions conducted using 2.5 equiv 2 and 5 mol% Ru(bipy)3Cl2 in the presence of LiBF4 and i-Pr2NEt in MeCN. Irradiation time using a 23 W compact fluorescent bulb at 30 cm was 4 h.

b

Isolated yields and diastereomer ratios are the averaged results of two reproducible experiments.

c

12 h irradiation.

d

24 h irradiation.