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NH
2
NH
2
Cl
-
OH
R
3
HN
O
R
2
HO
Ph
3-n
P
Ph
3-n
P
Ph
3-n
P
CO
2
Na
Ph
3-n
P
O
PPh
2
R
1
n
SO
3
Na
n = 1:
m-
TPPMS
n = 2:
m-
TPPDS
n = 3:
m-
TPPTS
n
CO
2
Na
n = 1:
m-
TPPMC
n = 2:
m-
TPPDC
n = 3:
m-
TPPTC
n
n
n = 1:
p-
TPPMC
n = 2:
p-
TPPDC
n = 3:
p-
TPPTC
n = 1:
m-
TPPMG
n = 2:
m-
TPPDG
n = 3:
m-
TPPTG
R
1
= OH, R
2
= OH, R
3
= H:
1
R
1
= OH, R
2
= H, R
3
= OH:
2
R
1
= NHAc, R
2
= OH, R
3
= H:
3
Scheme 14.2
H
3
C
Pd(OAc)
2
(2.5 mol %)
TXPTS (6.25 mol %)
H
2
O/CH
3
CN (1:1)
80 °C, 4 h
CO
2
H
Br
P
CH
3
+
CO
2
Na
3
MeO
MeO
SO
3
Na
79%
TXPTS
Scheme 14.3
NaO
3
S
Pd(OAc)
2
(2 m ol%)
BINAS (16 mol%)
NaOH, BuOH/H
2
O (3:2)
75 °C, 8 h
H
2
N
P
SO
3
Na
81%
+
O
O
O
O
2
P
SO
3
Na
Cl
NH
NaO
3
S
2
BINAS
Scheme 14.4
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