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Synlett 2021; 32(06): 631-635
DOI: 10.1055/s-0040-1706638
DOI: 10.1055/s-0040-1706638
letter
Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent
The authors thank the National Natural Science Foundation of China (21462038) for financial support of this work.
Abstract
An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706638.
- Supporting Information
Publikationsverlauf
Eingereicht: 10. Oktober 2020
Angenommen nach Revision: 16. November 2020
Artikel online veröffentlicht:
14. Dezember 2020
© 2020. Thieme. All rights reserved
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- 21 Diarylethynes 2a–r: General Procedure The appropriate aryldiazonium tetrafluoroborate 1 (0.4 mmol), CaC2 (77 mg, 1.2 mmol), Pd(PPh3)4 (23 mg, 0.02 mmol), CuI (8 mg, 0.04 mmol), NaI (180 mg, 1.2 mmol), and H2O (173 mg, 9.6 mmol) in DES (1:2 choline chloride–urea) (4 mL) were stirred at r.t. for 5 h. When the reaction was complete (TLC), H2O (2 mL) and EtOAc (2 mL) were added. The resulting mixture was subjected to ultrasonication for 5 min, then filtered to remove solids. The liquor was extracted with EtOAc (3 × 10 mL), and the extracts were washed with saturated brine (3 × 10 mL). The resulting organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, PE–EtOAc). Diphenylethyne (2a) White solid; yield: 29.5 mg (83%); mp 59–61 °C. 1H NMR (600 MHz, CDCl3): δ = 7.53 (dd, J = 8.0, 2.0 Hz, 4H), 7.35–7.33 (m, 6 H). 13C NMR (100 MHz, CDCl3): δ = 131.6, 128.3, 128.2, 123.3, 89.3. HRMS (ESI): m/z [M + H]+ calcd for C14H11: 179.0855; found: 179.0852. Bis(4-ethoxyphenyl)ethyne (2j) Yellow solid; yield: 35.6 mg (67%); mp 163–166 °C. 1H NMR (600 MHz, CDCl3): δ = 7.42 (d, J = 8.8 Hz, 4 H), 6.84 (d, J = 8.7 Hz, 4 H), 4.04 (q, J = 7.0 Hz, 4 H), 1.41 (t, J = 7.0 Hz, 6 H). 13C NMR (150 MHz, CDCl3): δ = 158.7, 132.8, 115.6, 114.5, 87.9, 63.5, 14.7. HRMS (ESI): m/z [M + H]+ calcd for C18H19O2: 267.1380; found: 267.1382.