Palladium-Catalyzed Hydroarylation of Diazoacetic Ester

Igor D. Titanyuk; Irina P. Beletskaya

doi:10.1055/s-0032-1317793

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(3): 355-358
DOI: 10.1055/s-0032-1317793

letter

Palladium-Catalyzed Hydroarylation of Diazoacetic Ester

Igor D. Titanyuk*

Moscow State University, Department of Chemistry 119991, Leninskie Gory 1-3, Moscow, Russian Federation Fax: +7(495)9328846 eMail: i-titan@yandex.ru

,

Irina P. Beletskaya

Moscow State University, Department of Chemistry 119991, Leninskie Gory 1-3, Moscow, Russian Federation Fax: +7(495)9328846 eMail: i-titan@yandex.ru

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Abstract

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Abstract

The novel procedure for the Pd-catalyzed hydroarylation of α-diazoacetic ester is reported. In the presence of a catalytic amount of PdCl₂(PPh₃)₂ the three-component reaction of aryl iodides, ethyl diazoacetate, and formic acid proceeds smoothly resulting in the formation of a series of arylacetates.

Key words

hydroarylation - diazoacetic ester - arylacetates - palladium catalysis - cross-coupling

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Referenzen

References and Notes

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18 Typical Procedure for the Pd-Catalyzed Cross-Coupling between Aryl Iodides and EDA To a mixture of aryl iodide 1a–h (1 mmol), PdCl₂(PPh₃)₂ (35 mg, 0.05 mmol) in a Schlenk flask under argon atmosphere, Et₃N (254 mg, 2.5 mmol) and formic acid (69 mg, 1.5 mmol) in MeCN (3 mL) were added. The mixture was stirred and heated to 70 °C, then EDA (171 mg, 1.5 mmol) in MeCN (2 mL) was added in small portions for 40–60 min. The mixture was stirred at the same temperature until 1a–h disappeared (the total time of heating indicated in Table 2). The solvent was evaporated in vacuo. Purification of the mixture by column chromatography (EtOAc–hexane = 1:10 v/v) gave the pure compounds 2a–h.
19 Selected Data for Synthesized Compounds Compound 2a: colorless oil. ¹H NMR (400 MHz, CDCl₃): δ = 7.98 (d, 2 H, J = 7.2 Hz), 7.35 (d, 2 H, J = 7.2 Hz), 4.14 (q, 2 H, J = 7.0 Hz), 3.88 (s, 3 H), 3.65 (s, 2 H), 1.23 (t, 3 H, J = 7.1 Hz). ¹³C NMR (100 MHz, CDCl₃): δ = 170.8, 166.8, 139.3, 129.8, 129.3, 129.0, 61.0, 52.0, 41.3, 14.1. IR (film): 1733, 1615, 1290 cm^–1. Anal. Calcd for C₁₂H₁₄O₄: C, 64.85; H, 6.35. Found: C, 64.92; H, 6.39. Compound 2e: yellow oil. ¹H NMR (400 MHz, CDCl₃): δ = 8.14 (m, 2 H), 7.62 (m, 1 H), 7.51 (m, 1 H), 4.18 (q, 2 H, J = 7.0 Hz), 3.73 (s, 2 H), 1.27 (t, 3 H, J = 7.1 Hz). ¹³C NMR (100 MHz, CDCl₃): δ = 170.3, 148.2, 136.0, 135.6, 129.4, 124.4, 122.2, 61.4, 41.0, 14.1. IR (film): 1740, 1540, 1360 cm^–1. Anal. Calcd for C₁₀H₁₁NO₄: C, 57.41; H, 5.30; N, 6.70. Found: C, 57.48; H, 5.39; N, 6.75. Compound 2g: colorless oil. ¹H NMR (400 MHz, CDCl₃): δ = 8.52 (m, 2 H), 7.64 (d, 1 H, J = 7.8 Hz), 7.25 (m, 1 H), 4.16 (q, 2 H, J = 7.0 Hz), 3.61 (s, 2 H), 1.25 (t, 3 H, J = 7.1 Hz). ¹³C NMR (100 MHz, CDCl₃): δ = 170.6, 150.3, 148.5, 136.7, 129.8, 128.5, 123.3, 61.1, 38.5, 14.1. IR (film): 1730, 1600 cm^–1. Anal. Calcd for C₉H₁₁NO₂: C, 65.44; H, 6.71; N, 8.48. Found: C, 65.54; H, 6.66; N, 8.57.

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