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of Tf2O and PPh3O provided phenanthridine 6 in
87%.[15a] Finally, phenanthridinone 7 was prepared by
an intramolecular cyclization of biaryl carbamate
(Exp. B).[15b] Phenanthridine and phenanthridinone
derivatives are often present in various natural prod-
ucts and are biologically active molecules.[15]
In conclusion, we have successfully developed
a new method for the synthesis of ortho-arylated ani-
lide derivatives in a highly regioselective manner
from N-phenylpivalamides and iodobenzenes through
À
a rhodium-catalyzed C H activation process. Further
investigation to better understand this transformation
and expand the application of this methodology is un-
derway.
Experimental Section
Experimental Details: A sealed tube (20 mL) containing
[{RhCp*Cl2}2] (2.1 mg, 2.0 mol%), N-phenylpivalamide 1a
(30 mg, 0.17 mmol), AgSbF6 (14.6 mg, 25 mol%) and AgO-
COCF3 (37.5 mg, 1 equiv) was evacuated and purged with
nitrogen gas three times. Then, DCE (3.00 mL) was added
by syringe. After 5 min, iodobenzene 2a (69.4 mg,
0.34 mmol) was added and the reaction mixture was stirred
at 1208C for 24 h and then diluted with dichloromethane.
The mixture was filtered through a pad of Celite and silica
gel and washed with dichloromethane. The filtrate was con-
centrated and the residue was purified on a silica gel
column using hexane/ethyl acetate as eluent to afford the
desired product 3a.
Acknowledgements
We thank the Ministry of Science and Technology of the Re-
public of China (NSC 102-2628-M-007-005 and NSC 102-
2633-M-007-002) for support of this research.
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