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. Author manuscript; available in PMC: 2011 Jul 6.
Published in final edited form as: J Am Chem Soc. 2009 Dec 2;131(47):17423–17429. doi: 10.1021/ja9081815

Table 3.

Cu- and Pd- catalyzed arylation of 4-aminophenolsa

graphic file with name nihms158545f10.jpg
a

Isolated yield, average of two runs.

b

2% of the N-arylated product was observed.

c

ArBr.

d

ArCl.

e

80 min.

f

3 h.

g

24 h.

h

K2CO3, t-BuOH.

i

1 % 8.

j

1 % 8, 24 h.

k

1% 8, K2CO3, t-BuOH, 24 h.

l

48 h.

m

ArCl, K2CO3, t-BuOH, 3 h.

n

0.5 mmol scale.

o

16 % of the N-arylated product was observed.

p

3% of the N-arylated product was observed.

q

1 % 7, 1% 8, K2CO3, t-BuOH, 110 °C, 24 h.