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. Author manuscript; available in PMC: 2012 Aug 3.
Published in final edited form as: J Am Chem Soc. 2011 Jul 8;133(30):11492–11495. doi: 10.1021/ja205017e

Table 2.

Product distributions from the oxidative coupling of lithium enolatesa

Ketone A Ketone B Heterocoupled Product Product Ratiob Yield (%)c,d
6 7 graphic file with name nihms-310689-t0011.jpg 13.8 : 1 62
8 7 graphic file with name nihms-310689-t0012.jpg 12.8 : 1 58
9 7 graphic file with name nihms-310689-t0013.jpg 12.4 : 1 62
10 7 graphic file with name nihms-310689-t0014.jpg 7.0 : 1 46
11 7 graphic file with name nihms-310689-t0015.jpg 3.0 : 1 47
a

[A] = [B] = 0.12 M in THF, [LiHMDS] = 0.26 M in THF, [I2] = 0.12 M in THF.

b

Ratios (heterocoupled product:homodimer of 7) were determined by 1H NMR.

c

Determined by 1H NMR with ± 3 % error.

d

15–25% of ketone A was recovered in these reactions.