Journal
ACS CATALYSIS
Volume 6, Issue 3, Pages 1691-1700Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b00027
Keywords
palladium-catalyzed; arylation; domino reactions; indoles; density functional calculations
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Funding
- Spanish Ministerio de Economia y Competitividad, Fondos Europeos para el Desarrollo Regional (MINECO-FEDER) [CTQ2012-31391, CTQ2013-44303-P]
- Spanish Ministerio de Economia y Competitividad, Fondos Europeos para el Desarrollo Regional (MINECO-FEDER) (Red de Excelencia Consolider) [CTQ2014-51912-REDC]
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A novel four-step domino process for the synthesis of 3-[2-(aryl/alkylsulfonyl)ethyl]indoles starting from readily available 2-iodoanilines is reported. The domino reaction is based on the intramolecular palladium-catalyzed alpha-arylation of sulfones, which was combined with both intermolecular aza-Michael and Michael addition reactions using vinyl sulfones as the electrophile. The domino process produced good yields and tolerated the presence of substituents with different electronic properties on the aniline ring. In addition, density functional theory (DFT) calculations were carried out to gain more insight into the formation of the observed indole derivatives.
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