Mono- and Biscouplings Using Triarylbismuths for the Atom-Efficient Arylations of Functionalized Furans under Palladium Catalysis

Maddali L. N. Rao; Dheeraj K. Awasthi; Jalindar B. Talode

doi:10.1055/s-0032-1316567

Synlett, Table of Contents

Synlett 2012; 23(13): 1907-1912
DOI: 10.1055/s-0032-1316567

letter

Mono- and Biscouplings Using Triarylbismuths for the Atom-Efficient Arylations of Functionalized Furans under Palladium Catalysis

Maddali L. N. Rao*

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208 016, India, Fax: +91(512)2597532 Email: maddali@iitk.ac.in

,

Dheeraj K. Awasthi

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208 016, India, Fax: +91(512)2597532 Email: maddali@iitk.ac.in

,

Jalindar B. Talode

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208 016, India, Fax: +91(512)2597532 Email: maddali@iitk.ac.in

› Author Affiliations

Abstract

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Abstract

Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one hour).

Key words

palladium - triarylbismuths - 2-bromofurans - cross-coupling - arylation

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References

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19 Representative Procedure for the Cross-Coupling Reaction of 5-Bromofurfural with Ph₃Bi The reaction was performed in a hot oven-dried Schlenk tube with the following reaction conditions: 5-bromofurfural (0.825 mmol, 144 mg, 3.3 equiv), Ph₃Bi (0.25 mmol, 110 mg, 1.0 equiv), Pd(OAc)₂ (0.025 mmol, 5.6 mg, 0.1 equiv), Cs₂CO₃ (0.75 mmol, 244 mg, 3.0 equiv), Ph₃P (0.1 mmol, 26 mg, 0.4 equiv), dry NMP (3 mL), 90 °C, 1 h. After the reaction, it was worked up following the procedure given in ref. 16 to obtain the product 2.1.^3d Analytical Data Orange liquid (0.115 g, 89%). ¹H NMR (500 MHz, CDCl₃): δ = 9.63 (1 H, s, CHO), 7.80–7.82 (m, 2 H, CH_ar), 7.30–7.44 (m, 4 H, CH_ar), 6.83 (d, 1 H, J = 3.7 Hz, CH_ar) ppm. ¹³C NMR (125 MHz, CDCl₃): δ = 177.2, 159.4, 152.0, 129.7, 128.9, 125.3, 123.6, 107.7 ppm. IR (KBr): ν = 1671, 1435, 1210, 1040, 971, 933, 887, 784, 671 cm^–1. ESI-HRMS: m/z calcd for C₁₁H₉O₂ [MH] ⁺ : 173.0603; found: 173.0606. Analytical data of all the products with spectra for 2.1–2.10 and 3.1–3.8 are given in the Supporting Information.

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21 Biscouplings of 2,5-dibromofuran were performed in a hot oven-dried Schlenk tube with the reaction conditions: 2,5-dibromofuran (0.29 mmol, 1.16 equiv), Ar₃Bi (0.25 mmol, 1 equiv), Cs₂CO₃(0.75 mmol, 3 equiv), Pd(OAc)₂ (0.025 mmol, 0.1 equiv), Ph₃ P (0.1 mmol. 0.4 equiv), dry NMP (3 mL), 90 °C, 1 h. The workup procedure was followed as given in ref. 16 to obtain 2,5-diphenylfuran (5.1).²⁵ Analytical Data White solid (0.051 g, 80%), mp 67–69 °C. ¹H NMR (500 MHz, CDCl₃): δ = 7.76 (d, 4 H, J = 8.3 Hz, CH_ar), 7.42 (t, 4 H, J = 7.8 Hz, CH_ar), 7.26–7.30 (m, 2 H, CH_ar), 6.75 (s, 2 H, CH_ar) ppm. ¹³C NMR (125 MHz, CDCl₃): δ = 153.3, 130.8, 128.7, 127.3, 123.7, 107.2 ppm. IR (KBr): ν = 1597, 1473, 1020, 914, 796, 757, 686 cm^–1. ESI-HRMS: m/z calcd for C₁₆H₁₂O [M] ⁺ : 220.0888; found: 220.0885. Analytical data of all the products with spectra for 5.1–5.9 are given in the Supporting Information.
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Supplementary Material

Supporting Information