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Synlett 2016; 27(13): 1945-1948
DOI: 10.1055/s-0035-1562104
DOI: 10.1055/s-0035-1562104
letter
Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes
Autoren
Weitere Informationen
Publikationsverlauf
Received: 03. März 2016
Accepted after revision: 01. April 2016
Publikationsdatum:
04. Mai 2016 (online)
Abstract
Described herein is a novel palladium-catalyzed C–N bond-formation reaction employing aryltrimethylgermanes as the new arylating reagents. Primary/secondary amines or even amides could be smoothly arylated to provide the corresponding N-arylation products in moderate to excellent yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562104.
- Supporting Information (PDF) (opens in new window)
-
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- 10 Representative Procedure A Schlenk reaction tube was charged with phenyltrimethylgermane (2a, 194.9 mg, 1.0 mmol), 4-methoxyaniline (1m, 147.9 mg, 1.2 mmol), Pd(OAc)2 (11.2 mg, 5 mol%), Ph3P (13.1 mg, 5 mol%), NaOAc (164.1 mg, 2.0 mmol), toluene (2.0 mL), under argon atmosphere at 100 °C for 12 h. After completion of the reaction, as indicated by TLC, the reaction mixture was extracted with Et2O (3 × 10 mL). The combined organic layer was washed by water and dried by Na2SO4. The solvent was removed in vacuo, and the residue was purified by a short column chromatography (silica gel 300–400 mesh, PE–EtOAc = 8:1) to give 3m in 87% isolated yield (173 mg); mp 102–103 °C. 4-Methoxy-N-Phenylaniline (3m) 1H NMR (300 MHz, CDCl3): δ = 7.25–7.18 (m, 3 H), 7.09–7.05 (m, 2 H), 6.92–6.83 (m, 4 H), 5.49 (s, 1 H), 3.81 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 135.7, 129.3, 124.3, 122.2, 119.5, 115.6, 114.6, 114.1, 55.6. MS (EI): m/z = 212. Anal. Calcd for C13H13NO: C, 78.35; H, 6.59; N, 7.02. Found: C, 78.22; H, 6.41; N, 6.95.