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Synlett 2018; 29(18): 2427-2431
DOI: 10.1055/s-0037-1611001
DOI: 10.1055/s-0037-1611001
letter
Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents
Financial support from the University of Potsdam is gratefully acknowledged.Further Information
Publication History
Received: 17 August 2018
Accepted after revision: 07 September 2018
Publication Date:
11 October 2018 (online)
Abstract
Arylindium and isolated triarylbismuth compounds generated in situ react as nucleophiles with arenediazonium salts in palladium-catalyzed cross-coupling reactions to give substituted biphenyls.
Key words
palladium catalysis - cross-coupling - arenediazonium salts - organobismuth compounds - organoindium compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611001.
- Supporting Information
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- 51 Methyl 4-Hydroxy-3′-methoxybiphenyl-3-carboxylate (4cf); Typical Example The diazonium salt 3f (134 mg, 0.50 mmol), triarylbismuthane 7c (265 mg, 0.50 mmol, 1.0 equiv), Pd(acac)2 (15.2 mg, 0.05 mmol, 10 mol%), and NaOAc (123 mg, 1.50 mmol, 3.0 equiv) were suspended in MeCN (0.5 mL, 1.0 M), and the mixture was stirred for 16–18 h at r.t. The mixture was then diluted with EtOAc (30 mL), washed with H2O (30 mL), dried (MgSO4), and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, PE–EtOAc) to give a colorless oil; yield: 66 mg (51%, 0.26 mmol). IR (ATR): 2999 (bw), 1738 (w), 1675 (m), 1204 (s), 1170 (m) cm–1. 1H NMR (500 MHz, CDCl3): δ = 10.78 (s, 1 H), 8.07 (d, J = 2.2 Hz, 1 H), 7.70 (dd, J = 8.6, 2.2 Hz, 1 H), 7.35 (t, J = 7.9 Hz, 1 H), 7.13 (d, J = 7.7 Hz, 1 H), 7.09–7.03 (m, 2 H), 6.88 (dd, J = 8.2, 2.2 Hz, 1 H), 3.98 (s, 3 H), 3.87 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 170.7, 161.2, 160.2, 141.6, 134.6, 132.4, 130.0, 128.4, 119.3, 118.2, 112.7, 112.6, 112.4, 55.5, 52.5. HRMS (ESI): m/z [M + Na]+ calcd for C15H14NaO4: 281.0784; found: 281.0787.