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Synlett

Volumn , Issue 5, 2009, Pages 0808-0812

Palladium-catalyzed direct C-3 arylations of indoles with an air-stable HASPO

(2) Ackermann, Lutz a Barfüßer, Sebastian a

a UNIVERSITY OF GÖTTINGEN (Germany)

Author keywords

C H bond functionalization; Heteroarenes; Indoles; Palladium; Regioselectivity

Indexed keywords

EID: 62349113696 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087951 Document Type: Article

Times cited : (71)

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46
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- Representative Procedure, Synthesis of 3a (Table 1, Entry 10) A suspension of Pd(OAc)2 (5.6 mg, 0.025 mmol, 5.0 mol, and 4h (28.4 mg, 0.05 mmol, 10 mol, in dry dioxane (1 mL) was stirred for 30 min under N2 at ambient temperature. K2CO3 (207.0 mg, 1.50 mmol, indole (1a, 59.0 mg, 0.50 mmol, and 4-bromotoluene (2a, 106.0 mg, 0.62 mmol) were added, and the suspension was stirred at 95°C for 20 h. After the reaction mixture was cooled to ambient temperature, Et2O (50 mL) and brine (50 mL) were added. The aqueous phase was extracted with Et2O (2 x 50 mL, The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The remaining residue was purified by column chromatography on SiO2 (n-hexane-EtOAc, 10:1) to yield 3a (97.0 mg, 94, as a pale yellow solid; mp 107.4-108.3°C, 1H NMR 300 MHz, DMSO-d 6
- 19

51
- 62349136346
- Analytical Data Indole 3i: mp 80.3-82.2°C. 1H NMR (300 MHz, CDCl3, δ, 8.19 (br s, 1 H, 7.62 (t, J, 1.8 Hz, 1 H, 7.53 (dt, J, 7.7, 1.6 Hz, 1 H, 7.39-7.23 (m, 5 H, 6.93 (dd, J, 8.8, 2.4 Hz, 1 H, 3.88 (s, 3 H, 13C NMR (126 MHz, CDCl3, δ, 154.9 (Cq, 137.5 (C q, 134.6 (Cq, 131.7 (Cq, 130.0 (CH, 127.1 (CH, 125.9 (Cq, 125.8 (CH, 125.3 (CH, 123.0 (CH, 116.8 (C q, 112.7 (CH, 112.2 (CH, 101.5 (CH, 56.0 (CH3, IR (KBr, 3391, 1620, 1594, 1485, 1440, 1271, 1214, 791 cm-1. MS (EI, m/z, 257 (100, M, 242 (26, 215 (33, 178 (13, 152 (15) 128 (11, ESI-HRMS: m/z calcd for C15H13ClNO: 258.0680; found: 258.0682. Indole 3k: mp 134.1-135.8°C. 1H NMR (300 MHz, CDCl3, δ, 8.07 (br s, 1 H, 7.84 d, J, 7.9 Hz
- 16N: 222.1277; found: 222.1272.

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