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Synlett 2015; 26(15): 2127-2130
DOI: 10.1055/s-0034-1378826
DOI: 10.1055/s-0034-1378826
letter
Efficient Synthesis of Conjugated 1,3,4-Thiadiazole Hybrids through Palladium-Catalyzed Cross-Coupling of 2,5-Bis(4-bromophenyl)-1,3,4-thiadiazole with Boronic Acids
Further Information
Publication History
Received: 09 April 2015
Accepted after revision: 29 June 2015
Publication Date:
10 August 2015 (online)
Abstract
New derivatives of 2,5-bis(4-heteroarylphenyl)-1,3,4-thiadiazole were synthesized under Suzuki cross-coupling reactions from 2,5-bis(4-bromophenyl)-1,3,4-thiadiazole and commercially available boronic acids. Reactions were conducted in a two-phase solvent system in the presence of catalytic amounts of tetrakis(triphenylphosphine)palladium(0), cesium carbonate as a base, and tetrabutylammonium bromide playing a role of a phase-transfer catalyst.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378826.
- Supporting Information
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- 21 Representative Procedure for Suzuki Coupling 2,5-Bis(4-bromophenyl)-1,3,4-thiadiazole (3, 0.40 g, 1.00 mmol), the appropriate boronic acid (2.50 mmol), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol), TBAB (0.03 g, 0.10 mmol), and Cs2CO3 (3.26 g, 10.00 mmol) were treated with a combination of toluene (10 mL), H2O (6 mL), and EtOH (3 mL). The mixture was heated to 80 °C (oil bath) for 2–6 h (TLC monitoring). After cooling, CHCl3 (200 mL) was added and the mixture filtered through silica gel (20 mL). The filtrate was separated, the organic layer was dried over MgSO4 and then concentrated on a rotary evaporator. The residue was treated with a mixture of benzene–EtOAc (3:1). The solid precipitate was filtered off, washed with benzene–EtOAc (3:1) and air-dried to give the pure 2,5-disubstituted 1,3,4-thiadiazole. 3,5-Bis(4-biphenylyl)-1,3,4-thiadiazole (5a) White-pearl solid (0.34 g, 92% yield); mp 296–298 °C (lit.16 294–296 °C). 1H NMR (400 MHz, CDCl3): δ = 7.41 (t, J = 7.6 Hz, 1 H), 7.49 (t, J = 7.6 Hz, 2 H), 7.66 (d, J = 7.6 Hz, 2 H), 7.74 (d, J = 8.4 Hz, 2 H), 8.11 (d, J = 8.4 Hz, 2 H). 13C NMR (400 MHz, CDCl3): δ = 124.4, 127.1, 127.8, 128.1, 128.4, 129.0, 139.9, 143.9, 167.8. UV/Vis: λmax (CHCl3) 335.0 nm (ε · 10–3 60.3 cm–1 M–1). IR (ATR): ν = 3060, 3037, 2162, 1946, 1821, 1675, 1604, 1561, 1488, 1451, 1432, 1420, 1401, 1316, 1253, 1185, 1170, 1100, 1040, 1027, 1005, 997, 988, 910, 838, 760,718, 684 cm–1. Anal. Calcd for C26H18N2S: C, 79.97; H, 4.65; N, 7.17. Found: C, 79.99; H, 4.63; N, 7.21. HRMS: m/z calcd for [C26H18N2S + H+]: 391.1269; found: 391.1267.