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2005
Indole derivatives
R 0140
Direct C-Arylation of Free (NH)-Indoles and Pyrroles Catalyzed by Ar—Rh(III)
Assembled in situ. — Under optimized conditions concerning the phos34- 158 Complexes
phine ligand and the base, 2-arylated indoles and pyrroles are formed as the principal
products from the reaction of N-unsubstituted indoles and pyrroles with aryl iodides.
Remarkably, protic functional groups, such as carbamate, carboxamide, and sulfonamide, as well as halide, ketone, and ester groups are well tolerated. An important advance is the arylation in the presence of two acidic N—H bonds, exemplified by indoles
(Id)-(If). In addition, the method displays low moisture sensitivity and allows direct use
of commercial chemicals. It fails with 7-azaindole; N-methylpyrrole affords the
3-arylated product. — (WANG, X.; LANE, B. S.; SAMES*, D.; J. Am. Chem. Soc.
127 (2005) 14, 4996-4997; Dep. Chem., Columbia Univ., New York, NY 10027, USA;
Eng.) — Klein
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