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. Author manuscript; available in PMC: 2013 Mar 26.
Published in final edited form as: J Org Chem. 2011 May 19;76(12):5061–5073. doi: 10.1021/jo200746y

Table 3.

Comparison of Amphiphiles for Heck Couplings in Water

graphic file with name nihms298140u4.jpg
entry surfactantb yield (%)c
1 PTS 43
2 solutol 32
3 PTS at 40 °C 94
4 3 M NaCl, PTS/water 95
5 3M NaCl, solutol/water 46
6 “on water” 30
7 toluene 40
graphic file with name nihms298140u5.jpg
entry surfactantb yield (%)c
8 PTS 18
9 solutol 21
10 3 M NaCl, PTS/water 98
a

Conditions: tert-butyl acrylate (2 equiv), cat. 5 (2 mol %), Et3N (3 equiv) surfactant/H2O, 22 °C, 14 h.

b

5 wt. % used in all cases.

c

Chromatographically pure materials.