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. Author manuscript; available in PMC: 2014 Mar 19.
Published in final edited form as: J Am Chem Soc. 2012 Nov 28;134(49):19985–19988. doi: 10.1021/ja309409e

Table 3. Conjugate Addition Reactions of Secondary Alkyl Halides to Enonesa.

graphic file with name nihms425273u3.jpg
entry enone alkyl-X product yield (%)b
1 graphic file with name nihms425273t40.jpg graphic file with name nihms425273t41.jpg graphic file with name nihms425273t42.jpg 85
2c graphic file with name nihms425273t43.jpg graphic file with name nihms425273t44.jpg graphic file with name nihms425273t45.jpg 83
3 graphic file with name nihms425273t46.jpg graphic file with name nihms425273t47.jpg graphic file with name nihms425273t48.jpg 90
4 graphic file with name nihms425273t49.jpg graphic file with name nihms425273t50.jpg graphic file with name nihms425273t51.jpg 85
5 graphic file with name nihms425273t52.jpg graphic file with name nihms425273t53.jpg graphic file with name nihms425273t54.jpg 88
6 graphic file with name nihms425273t55.jpg graphic file with name nihms425273t56.jpg graphic file with name nihms425273t57.jpg 85
7 graphic file with name nihms425273t58.jpg graphic file with name nihms425273t59.jpg graphic file with name nihms425273t60.jpg 81
a

Conditions: alkyl-X (3 equiv), Zn powder (X = I) or Zn dust (X = Br) (4 equiv), TMEDA (2 equiv), 3 mol % [Cu], 5 mol % AuCl3, 0.5 mL 2 wt %-TPGS-750-M/H2O, rt, 24h.

b

Isolated, chromatographically purified.

c

Tetraethyl derivative of TMEDA used.