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. Author manuscript; available in PMC: 2015 Feb 7.
Published in final edited form as: J Org Chem. 2014 Jan 21;79(3):888–900. doi: 10.1021/jo401744b

Table 9.

Comparison of Nok vs. TPGS-750-M in Stille Couplings

graphic file with name nihms558965u8.jpg
Entry Aryl halide Partner Product TPGS-750-Ma yield(%) Noka yield(%) Time (h)
1 graphic file with name nihms558965t53.jpg graphic file with name nihms558965t54.jpg graphic file with name nihms558965t55.jpg 98 99 2
2 graphic file with name nihms558965t56.jpg graphic file with name nihms558965t57.jpg graphic file with name nihms558965t58.jpg 100 99 4
3 graphic file with name nihms558965t59.jpg graphic file with name nihms558965t60.jpg graphic file with name nihms558965t61.jpg 58 56 8
4 graphic file with name nihms558965t62.jpg graphic file with name nihms558965t63.jpg graphic file with name nihms558965t64.jpg 83 84 18
5 graphic file with name nihms558965t65.jpg graphic file with name nihms558965t66.jpg graphic file with name nihms558965t67.jpg 84 97 4
a

Isolated yields of chromatographically pure materials. Conditions: aryl bromide (0.25 mmol, 1 equiv), stannyl reagent (0.275 mmol, 1.1 equiv), catalyst Pd(t-Bu3P)2 (2 mol %), base DABCO (3 equiv), NaCl (1 equiv) and 2 wt % surfactant/H2O.