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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 6.

Sonogashira Couplings: Nok vs. TPGS-750-M

graphic file with name nihms558965u6.jpg
Entry Aryl halide Alkyne Product TPGS-750-Ma yield(%) Noka yield(%) Time (h)
1 graphic file with name nihms558965t26.jpg graphic file with name nihms558965t27.jpg graphic file with name nihms558965t28.jpg 98 98 24
2 graphic file with name nihms558965t29.jpg graphic file with name nihms558965t30.jpg graphic file with name nihms558965t31.jpg 94 95 28
3 graphic file with name nihms558965t32.jpg graphic file with name nihms558965t33.jpg graphic file with name nihms558965t34.jpg 97 90 2
4 graphic file with name nihms558965t35.jpg graphic file with name nihms558965t36.jpg graphic file with name nihms558965t37.jpg 93 93 15
a

Isolated yields of chromatographically pure materials. Reaction conditions: alkyl bromide (0.5 mmol, 1 equiv), boronic acid (0.65–1.00 mmol), XPhos (2.5 mol %), triethylamine (3 equiv), catalyst Pd(CH3CN)2Cl2 (2 mol %), and 2 wt % of surfactant/H2O.