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2‐(2‐Haloalkenyl)‐aryl Halides as Substrates for Palladium‐Catalysed Tandem CN Bond Formation: Efficient Synthesis of 1‐Substituted Indoles
Author(s) -
Willis Michael C.,
Brace Gareth N.,
Findlay Thomas J. K.,
Holmes Ian P.
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505484
Subject(s) - chemistry , amination , aryl , halide , tandem , palladium , catalysis , alkene , combinatorial chemistry , amine gas treating , aryl halide , medicinal chemistry , organic chemistry , alkyl , materials science , composite material
2‐(2‐Haloalkenyl)‐aryl halides, conveniently prepared in a single step from the corresponding o ‐halobenzaldehydes, are combined with amines under Pd catalysis to provide 1‐substituted indoles. All combinations of Br and Cl leaving groups can be employed, and a range of substituents on the arene, alkene and amine, can all be tolerated. The use of 1,3‐dichloro‐substituted arenes allows a third amination process to take place; these three‐component processes deliver the corresponding 4‐aminoindoles in good yields.