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. Author manuscript; available in PMC: 2016 Jun 19.
Published in final edited form as: J Org Chem. 2015 Jun 1;80(12):6012–6024. doi: 10.1021/acs.joc.5b00794

Table 4.

Visible-Light Photocatalytic Coupling of N-Phthalimidoyl Oxalate 3a with MVK in the Presence of Potential Stoichiometric Reductantsaa

Entry Reductant Yield of 5 (%)
1 graphic file with name nihms-746869-t0003.jpg 4 R = 4 82b
2 6 R = Me ND
3 7 R = Ph ND
4 graphic file with name nihms-746869-t0004.jpg 60c
5 graphic file with name nihms-746869-t0005.jpg 73c
6 graphic file with name nihms-746869-t0006.jpg ND
a

Conditions of eq 2 using i-Pr2NEt•HBF4; [3a] = 0.15 M.

b

Isolated yield after silica gel chromatography.

c

Yield measured by 1H NMR relative to an internal standard (1,4-dimethoxybenzene);

ND = not detected.