2013
DOI: 10.1055/s-0033-1340052
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Iron(II) Chloride–1,1′-Binaphthyl-2,2′-diamine (FeCl2–BINAM) Complex Catalyzed Domino Synthesis of Bisindolylmethanes from Indoles and Primary Alcohols

Abstract: Biologically important bisindolylmethanes are synthesized in a domino fashion by using an iron(II) chloride-(±)-1,1′-binaphthyl-2,2′-diamine [FeCl 2 -(±)-BINAM] complex as the catalyst. This method proceeds via oxidation of a primary alcohol into the corresponding aldehyde followed by nucleophilic addition of an indole in the presence of the catalyst. A reaction intermediate is synthesized separately and converted into the bisindolylmethane product under the same reaction conditions as support for the proposed… Show more

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Cited by 18 publications
(12 citation statements)
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“…R f = 0.30 (40:10 PE:EA); mp 139–140 o C, lit. mp 141–142 o C [43]; 1 H NMR (400 MHz, CDCl 3 ) δ 5.89 (1H, s), 6.67 (2H, dd, J = 2.4, 0.9 Hz), 7.00 (2H, td, J = 7.5, 1.0 Hz), 7.19 (2H, t, J = 7.9 Hz), 7.22–7.25 (1H, m), 7.28–7.30 (2H, m), 7.34–7.39 (4H, m), 7.40–7.43 (2H, m), 7.90 (2H, br s); 13 C NMR (100 MHz, CDCl 3 ) δ 40.2, 111.0, 119.3, 119.8, 120.0, 121.9, 123.6, 126.2, 127.1, 128.2, 128.7, 136.7, 144.0; HRMS (ESI+) calcd for C 23 H 19 N 2 [M+H] + 323.1543, found 323.1531 (error 3.7 ppm). All spectroscopic data were in agreement with the literature values.…”
Section: Methodsmentioning
confidence: 99%
“…R f = 0.30 (40:10 PE:EA); mp 139–140 o C, lit. mp 141–142 o C [43]; 1 H NMR (400 MHz, CDCl 3 ) δ 5.89 (1H, s), 6.67 (2H, dd, J = 2.4, 0.9 Hz), 7.00 (2H, td, J = 7.5, 1.0 Hz), 7.19 (2H, t, J = 7.9 Hz), 7.22–7.25 (1H, m), 7.28–7.30 (2H, m), 7.34–7.39 (4H, m), 7.40–7.43 (2H, m), 7.90 (2H, br s); 13 C NMR (100 MHz, CDCl 3 ) δ 40.2, 111.0, 119.3, 119.8, 120.0, 121.9, 123.6, 126.2, 127.1, 128.2, 128.7, 136.7, 144.0; HRMS (ESI+) calcd for C 23 H 19 N 2 [M+H] + 323.1543, found 323.1531 (error 3.7 ppm). All spectroscopic data were in agreement with the literature values.…”
Section: Methodsmentioning
confidence: 99%
“…24 Afterwards, reports on the C3-alkylation of indoles were presented with Ru-, [25][26][27][28] Ir-, 25,[29][30][31][32] Pd-, 26,33,34 Rh-, 25 and Pt-35 complexes as catalysts. In addition, homogeneous Fe-, [36][37][38][39][40][41][42] Mn-, 43 Ni- 44,45 and Cu-20,46-49 complexes have been reported to be effective in the C3-alkylation of indole. In contrast, in heterogeneous catalysis only Pt-based materials have been reported.…”
Section: Introductionmentioning
confidence: 99%
“…24 Sekar's group used an FeCl 2 /BINAM complex for domino synthesis of BIMs from indoles and primary alcohols. 25 Vu et al used CuFe 2 O 4 as a recyclable magnetic catalyst with Li-O t Bu for synthesis of BIMs at 80 °C. 26 Balaram et al 27 performed dehydrogenative coupling of alcohols with indoles using an air-stable NNN–Mn( ii ) pincer complex in 20 h at 120 °C.…”
Section: Introductionmentioning
confidence: 99%