Palladium catalyzed alkylation of indole via aliphatic C-H bond activation of tertiary amine

Tetrahedron Letters

Volumn 52, Issue 28, 2011, Pages 3579-3583

  Ramachandiran, K ^a   Muralidharan, D ^a   Perumal, P T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

1,1 Bis indolymethane; Alkylation of indole; C C coupling; C H activation; Palladium

Indexed keywords

ALIPHATIC COMPOUND; ALKANE; INDOLE; PALLADIUM; TERTIARY AMINE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 79958274984     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.110     Document Type: Article

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55. 2 (0.1 mmol) and tertiary amines (1.3 mmol) was stirred at 70 °C for 12 h under neat condition. The reaction mixture was dissolved in ethyl acetate and filtered through a plug of Celite. The residue was washed with ethyl acetate (2 × 20 mL). The filtrate was washed with 100 mL of water and 10 mL of 0.5 N HCl and the organic layer was collected. The aqueous phase was extracted with ethyl acetate (3 × 20 mL). The combined organic phase was washed with saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as eluent to afford the corresponding products and appropriate yield is shown in Table 2 and 3.
56. 2: C, 75.83; H, 6.94; N, 8.04; O, 9.18; Found: C, 75.92; H, 6.84; N, 8.15.