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Pd(0)‐Catalyzed Dearomative Diarylation of Indoles
Author(s) -
Petrone David A.,
Kondo Masaru,
Zeidan Nicolas,
Lautens Mark
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600118
Subject(s) - diastereomer , steric effects , catalysis , chemistry , combinatorial chemistry , ligand (biochemistry) , parallels , substrate (aquarium) , organic chemistry , operations management , biology , biochemistry , engineering , ecology , receptor
We have developed a protocol for a Pd(0)‐catalyzed dearomative syn 1,2‐diarylation of indoles using readily available boroxines (dehydrated boronic acids) as coupling partners. This reaction proceeds efficiently using P t Bu 3 as the ligand to divergently access to fused indolines while minimizing the extent of direct Suzuki coupling. The scope of the reaction is remarkably broad and all products are obtained as single diastereomers in moderate to excellent yields. We have also compiled data which parallels the steric and electronic properties of both substrate and boroxine with the propensity to undergo the desired dearomative process over direct Suzuki coupling.