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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 11.

Nok vs. TPGS-750-M in amination reactions

graphic file with name nihms558965u10.jpg
Entry Aryl halide Partner Product TPGS-750-Ma yield(%) Noka yield(%) Time (h)
1b graphic file with name nihms558965t72.jpg graphic file with name nihms558965t73.jpg graphic file with name nihms558965t74.jpg 95 91 21
2b graphic file with name nihms558965t75.jpg graphic file with name nihms558965t76.jpg graphic file with name nihms558965t77.jpg 75 75 10
  3c,d graphic file with name nihms558965t78.jpg graphic file with name nihms558965t79.jpg graphic file with name nihms558965t80.jpg 85 85 24
  4c,e graphic file with name nihms558965t81.jpg graphic file with name nihms558965t82.jpg graphic file with name nihms558965t83.jpg 96 93 24
a

Isolated yields.

b

Reaction conditions: aryl bromide (1.00 mmol, 1 equiv), toluidine (1.20 mmol, 1.2 equiv), catalyst [(π-allyl)PdCl]2 (0.5 mol %), cBRIDP (2 mol %), K-O-t-Bu (1.5 equiv) and 2 wt % of surfactant/H2O; at rt.

c

Na-O-t-Bu (1.5 equiv); reaction was run at 50 °C, 24 h using [(π-allyl)PdCl]2 (0.5 mol %), cBRIDP (2 mol %), K-O-t-Bu (1.5 equiv) and 2 wt % of surfactant/H2O.

d

Reaction conditions: aryl bromide (1.00 mmol, 1 equiv), t-butyl carbamate (1.50 mmol, 1.5 equiv).

e

Reaction conditions: aryl bromide (0.50 mmol, 1 equiv), ethyl carbamate (0.60 mmol, 1.2 equiv).