Pd(0)-Catalyzed Dearomative Diarylation of Indoles

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 PtBu3 as the ligand to divergently access to fused indolines while minimizing the...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-04, Vol.22 (16), p.5684-5691
Main Authors: Petrone, David A., Kondo, Masaru, Zeidan, Nicolas, Lautens, Mark
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemistry
Coupling
C−C coupling
Dehydration
diastereoselectivity
Electronic properties
heterocycles
Heterocyclic aromatic compounds
homogeneous catalysis
Indoles
Ligands
palladium
Substrates
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Summary: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 PtBu3 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. In‐dole zone: N‐Benzoyl indoles can be dearomatized by a fully syn‐selective Pd(0)‐catalyzed intramolecular diarylation using aryl and vinyl boroxines as coupling partners (see scheme). This operationally simple method provides an easy and highly divergent access to complex indoline‐containing tetracyclic products.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201600118