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Me
O
Ph
Me
O
Me
OH
RuH
2
(CO)(PPh
3
)
3
(0.02 mmol)
toluene, reflux
Me
B
+
+
OO
Me
Ph
1mmol
2mmol
1mmol
1mmol
47%
82%
Scheme 12.84 Ortho-arylation of aromatic ketones.
O
Ph
R
Ph
O
R
B
R
RuH
2
(CO)(PPh
3
)
3
(0.02 mmol)
pinacolone, reflux
+
OO
R
n
n
1.2-1.5 equiv
R= H, Ar, alkyl
Scheme 12.85 Ortho-arylation of cyclic aromatic ketones.
Intermolecular Competition
Me
Me
Me
O
Me
O
Me
Me
0.5 mmol
RuH
2
(CO)(PPh
3
)
3
(0.02 mmol)
toluene(1mL),reflux
+
+
OMe
D
O
O
Me
Me
Me
D
Me
Me
Me
B
OMe
Me
Me
D
O
D
D
D
0.5 mmol
co nversion -
40% - 1.06
47% - 1.09
O
D
k
H
/
k
D
0.5 mmol
D
D
OM e
Intramolecular Competition
Me
Me
Me
H
O
H
O
RuH
2
(CO)(PPh
3
)
3
(0.02 mmol)
toluene(1 mL), reflux
Me
Me
Me
+
OMe
O
Me
D
Me
Me
Me
Me
B
OMe
1 mmol
D
O
0.5 mmol
O
conversion -
k
H
/
k
D
50% - 1.41
75% - 1.49
OMe
Scheme 12.86
Isotope labeling experiment.
bond, it is more likely that Ru coordinated to the ketonic oxygen prior to the
C-H activation.
12.4.4 Green Protocol
Most Ru-catalyzed reactions lack operational simplicity owing to the in-
volvement of hazardous or anaerobic conditions. In order to develop a more
sustainable protocol, Ackermann and Potukuchi
reported the direct
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