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. Author manuscript; available in PMC: 2016 Mar 11.
Published in final edited form as: J Am Chem Soc. 2015 Mar 3;137(9):3338–3351. doi: 10.1021/ja512690x

Table 1.

Evaluation of Reaction Conditionsa

graphic file with name nihms688285u1.jpg
Entry Solvent Additive % Yield of 2ab
1 t-AmylOH no 45
2 t-AmylOH TEMPO 40
3c t-AmylOH no   N.R.
4 Toluene no 30
5 CH3CN no 35
6 1,4-Dioxane no 50
7 DCE no 43
8 DMF no 40
9 CF3CH2OH no 60
10 HFIP no   76(86)d
11 DCE TFA 75
a

Conditions: Substrate 1 (0.1 mmol), Pd(OAc)2 (10 mol%), AgOAc (0.2 mmol), p-Tol–I (0.15 mmol), Ligand L1 (20 mol%), solvent (1.0 mL), 75 °C, 24 h.

b

Determined by 1HNMR analysis of the crude product using CH2Br2 as an internal standard, and the yield is based on the amide and ester.

c

Reaction run at 60 °C.

d

Combined 76% mono- and 10% di-arylated products determined by crude 1HNMR.