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“On Water” Direct and Site‐Selective Pd‐Catalysed CH Arylation of (NH)‐Indoles
Author(s) -
Joucla Lionel,
Batail Nelly,
Djakovitch Laurent
Publication year - 2010
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.201000512
Subject(s) - chemistry , regioselectivity , halide , indole test , catalysis , aryl , palladium , combinatorial chemistry , base (topology) , medicinal chemistry , stereochemistry , organic chemistry , alkyl , mathematical analysis , mathematics
This communication describes the development of a versatile catalytic system based on palladium(II) acetate/bis(diphenylphosphino)methane [Pd(OAc) 2 /dppm] that works “on water” giving site‐selective CH arylation of (NH)‐indoles without protecting or directing groups. Remarkably, the control of regioselectivity was achieved by small changes in the “extra‐catalytic” base/halide partners. These innovative methodologies allow a high‐yielding access to both C2 and C3‐arylindoles, as well as 2,3‐diarylindoles, and display high chemo/regioselectivities and structural versatility with regard to either indole or aryl moieties.