120
4.2 Oxidative Radical C-C Couplings Through Cascade
Process
Oxidative radical C-C couplings could be extended to synthesis more complex compounds through C-C coupling/cyclization process, which provides an access to different aromatic compounds.
The reaction of isonitrile with simple alkanes can proceed through the sequential
addition of alkyl radical/intramolecular cyclization of isonitrile, providing a convenient access to a series of 6-alkylated phenanthridines (Scheme 4.37). Using CuF 2
+
CH 3 CN
80 °C, 10 h
OMe
OMe
MeO
H
Ar 3
(Ar-H)
Ar
3
Ar
Ar
Ar
Ar
Br
67%
Ar
Ar
Cl
66%
Ar
Ar
F
48%
Ar
Ar
58%
Br
+
20 mol% FeCl 3
2 equiv DDQ
CH 3 CN
80 °C, 10 h
OMe
OMe
MeO
H
Ar 2
Ar 1
OMe
OMe
MeO
Ar
2
Ar
1
Ar
(Ar-H)
78%
Ar
69%
Cl
Cl
Ar
40%
F 3 C
CF 3
Ar
72% (E/Z=52:48)
Br
Cl
Ar
66% (E/Z=54:46)
Cl
Ar
73% (E/Z=60:40)
Cl
20 mol% FeCl 3
2 equiv DDQ
Scheme 4.35 Oxidative coupling of arenes and alkenes
W. Liu
4.2 Oxidative Radical C-C Couplings Through Cascade
Process
Oxidative radical C-C couplings could be extended to synthesis more complex compounds through C-C coupling/cyclization process, which provides an access to different aromatic compounds.
The reaction of isonitrile with simple alkanes can proceed through the sequential
addition of alkyl radical/intramolecular cyclization of isonitrile, providing a convenient access to a series of 6-alkylated phenanthridines (Scheme 4.37). Using CuF 2
+
CH 3 CN
80 °C, 10 h
OMe
OMe
MeO
H
Ar 3
(Ar-H)
Ar
3
Ar
Ar
Ar
Ar
Br
67%
Ar
Ar
Cl
66%
Ar
Ar
F
48%
Ar
Ar
58%
Br
+
20 mol% FeCl 3
2 equiv DDQ
CH 3 CN
80 °C, 10 h
OMe
OMe
MeO
H
Ar 2
Ar 1
OMe
OMe
MeO
Ar
2
Ar
1
Ar
(Ar-H)
78%
Ar
69%
Cl
Cl
Ar
40%
F 3 C
CF 3
Ar
72% (E/Z=52:48)
Br
Cl
Ar
66% (E/Z=54:46)
Cl
Ar
73% (E/Z=60:40)
Cl
20 mol% FeCl 3
2 equiv DDQ
Scheme 4.35 Oxidative coupling of arenes and alkenes
W. Liu