Palladium-Catalyzed Arylation
of the THP Derivative of (Z)-2-Butene-1,4-diol with
Arenediazonium Salts and the Synthesis of β-Aryl-γ-butyrolactones

Sandro Cacchi; Giancarlo Fabrizi; Antonella Goggiamani; Alessio Sferrazza

doi:10.1055/s-0028-1087959

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Synlett 2009(6): 973-977
DOI: 10.1055/s-0028-1087959

LETTER

Palladium-Catalyzed Arylation of the THP Derivative of (Z)-2-Butene-1,4-diol with Arenediazonium Salts and the Synthesis of β-Aryl-γ-butyrolactones

Sandro Cacchi*, Giancarlo Fabrizi, Antonella Goggiamani, Alessio Sferrazza
Dipartimento di Chimica e Tecnologie del Farmaco, Università degli Studi ‘La Sapienza’, P. le A. Moro 5, 00185 Rome, Italy
Fax: +39(06)49912780; e-Mail: sandro.cacchi@uniroma1.it;

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Publication History

Received 16 December 2008
Publication Date:
16 March 2009 (online)

Abstract
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Abstract

The reaction of arenediazonium tetrafluoroborates with the THP derivative of (Z)-2-butene-1,4-diol in the presence of Pd(OAc)₂ in MeOH at 35 ˚C gives 4-aryl-2-methoxytetrahydrofurans in good to high yields. The reaction tolerates a variety of useful functional groups including ester, keto, cyano, nitro, chloro, and bromo functionalities as well as ortho substituents. Based on this process, γ-aryl-β-butyrolactone derivatives can be prepared via a sequential palladium-catalyzed arylation-cyclization-oxidation protocol that omits the isolation of 4-aryl-2-methoxytetrahydrofuran intermediates.

Key words

arenediazonium salts - palladium - Mizoroki-Heck reaction - tetrahydrofurans - allylic alcohols

References and Notes

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8

The stereochemistry of 5b was assigned by NMR analysis. That of the other 4-aryl-2-methoxytetrahydrofuran derivatives has been assigned based on these data.

11

Preparation of 4-Aryl-2-methoxytetrahydrofuran (5) via Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates 2 with the THP Derivative of ( Z )-2-Buten-1,4-diol (6) - Typical Procedure To a stirred solution of 6 (128.2 mg, 0.50 mmol) and Pd(OAc)₂ (5.6 mg, 0.025 mmol) in anhyd MeOH (4.0 mL), 2a (221.9 mg, 1.0 mmol) was added at r.t. under argon. The reaction mixture was warmed at 35 ˚C and stirred for 1 h (the reactor was protected from light with aluminium film). After cooling, the reaction mixture was diluted with Et₂O, washed with a sat. NaHCO₃ solution, dried over Na₂SO₄, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel [n-hexane-EtOAc, 75:25 (v/v)] to afford 75.2 mg (72% yield) of 5a as an approximately 60:40 diastereomeric mixture. The cis-isomer was isolated and characterized.
Oil. IR (neat): 2940, 1606, 1077 cm^-¹. ^¹H NMR (400 MHz, CDCl₃): δ = 7.25 (d, J = 8.6 Hz, 2 H), 6.87 (d, J = 8.6 Hz,
2 H), 5.19-5.15 (dd, J ₁ = 5.5 Hz, J ₂ = 3.0 Hz, 1 H), 4.17 (t, J = 8.0 Hz, 1 H), 3.81 (s, 3 H), 3.76-3.71 (m, 1 H), 3.45 (s, 3 H), 3.39-3.32 (m, 1 H), 2.70-2.52 (m, 1 H), 2.00-1.85 (m, 1 H). ^¹³C NMR (100.6 MHz, CDCl₃): δ = 158.4, 133.2, 128.7, 114.0, 110.8, 105.9, 73.2, 55.3, 55.0, 43.6, 41.2. MS: m/z (%) = 208 (18) [M⁺], 177 (22), 147 (68).

12

Preparation of β-Aryl-γ-butyrolactones 13 from Arenediazonium Tetrafluoroborates 2 and the THP Derivative of ( Z )-2-Buten-1,4-diol (6) via a Sequential Palladium-Catalyzed Arylation-Cyclization-Oxidation Protocol - Typical Procedure To a stirred solution of 6 (128.2 mg, 0.50 mmol) and Pd(OAc)₂ (5.6 mg, 0.025 mmol) in anhyd MeOH (4.0 mL), 2b (250.0 mg, 1.0 mmol) was added at r.t. under argon. The reaction mixture was warmed at 35 ˚C and stirred for 45 min (the reactor was protected from light with aluminium film). After this time, the reaction mixture was diluted with Et₂O, washed with a sat. NaHCO₃ solution, dried over Na₂SO₄, and concentrated under reduced pressure. The residue was filtrated through a short bed of SiO₂ and concentrated under reduced pressure. The crude was dissolved in CH₂Cl₂ (3 mL) and MCPBA (123.3 mg, 0.5 mmol; a commercially available 70% MCPBA was used) and BF₃˙OEt₂ (25 µL, 0.2 mmol) were added. The cloudy reaction mixture was allowed to stir at r.t. for 24 h and then poured into an NaHSO₃ aq solution. The organic layer was removed, and the aqueous layer was washed with CH₂Cl₂. The organic layer was washed with aq NaHCO₃ , dried over Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel
[n-hexane-EtOAc, 75:25 (v/v)] to afford 81.4 mg (74%)
of 13b.
Mp 78-80 ˚C. IR (KBr): 1778, 1714, 1282, 1012 cm^-¹. ^¹H NMR (400 MHz, CDCl₃): δ = 8.02 (d, J = 8.3 Hz, 2 H), 7.31 (d, J = 8.3 Hz, 2 H), 4.68 (dd, J ₁ = 8.8 Hz, J ₂ = 7.9 Hz, 1 H), 4.28 (dd, J ₁ = 8.9 Hz, J ₂ = 7.9 Hz, 1 H), 3.90 (s, 3 H), 3.86 (qp, J = 8.3 Hz, 1 H), 2.96 (dd, J ₁ = 9.1 Hz, J ₂ = 8.8 Hz, 1 H), 2.68 (dd, J ₁ = 8.8 Hz, J ₂ = 17.2 Hz, 1 H). ^¹³C NMR (100.6 MHz, CDCl₃): δ = 175.9, 166.5, 144.7, 130.4, 129.7, 126.8, 73.6, 52.2, 41.0, 35.5. MS: m/z (%) = 220 (14) [M⁺], 162 (59), 131 (100), 77 (89).