Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions

Zhiyuan Yang; Pei-Xue Gong; Junjie Chen; Jie Zhang; Xu Gong; Wei Han

doi:10.1055/a-1511-0435

Synlett, Table of Contents

Synlett 2021; 32(12): 1207-1212
DOI: 10.1055/a-1511-0435

letter

Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions

Zhiyuan Yang‡

^aJiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China

,

Pei-Xue Gong‡

^aJiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China

,

Junjie Chen

^aJiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China

,

Jie Zhang

^aJiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China

,

Xu Gong

^aJiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China

,

Wei Han ∗

^aJiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing 210023, P. R. of China

^bJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing 210023, P. R. of China

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Abstract

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Abstract

A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.

Key words

platinum catalysis, vinyl iodides, arylboronic acids, chalcones, enones, Suzuki–Miyaura reaction

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References

References and Notes

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10 Poly(ethylene glycol) (PEG) is often used as a good phase-transfer agent. This property favors gas–liquid–solid multiphase catalytic reactions. Additionally, PEG is a highly polar solvent that is capable of strongly solvating polar molecules such as carbon monoxide to reduce mass-transfer resistance. These two positive properties probably permit PEG to show excellent performance in the current transformation.
11 (2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-one (3aa); Typical Procedure A 25 mL flask was charged with Pd(OAc)₂ (0.005 mmol, 1.2 mg), 1-[(E)-2-iodovinyl]-4-methoxybenzene (1a; 0.25 mmol, 65.0 mg), PhB(OH)₂ (2a; 0.375 mmol, 45.8 mg), K₃PO₄ (0.25 mmol, 54.7 mg), and PEG-400 (2.0 g), and was then subjected to standard cycles of evacuation and backfilling with dry pure CO. The mixture was stirred at RT and atmospheric pressure (CO balloon) for 3 h. The mixture was then extracted with Et₂O (3 × 15 mL) and the organic phases were combined and concentrated under reduced pressure. The crude product was purified by column chromatography [silica gel, PE–Et₂O (100:1 to 10:4)] to give a light-yellow solid; yield: 54 mg (92%; E/Z >99:1). ¹H NMR (400 MHz, CDCl₃): δ = 8.04 (d, J = 8.4 Hz, 2 H), 7.82 (d, J = 15.6 Hz, 1 H), 7.63 (d, J = 8.4 Hz, 2 H), 7.59 (d, J = 7.2 Hz, 1 H), 7.52 (t, J = 7.6 Hz, 2 H), 7.45 (d, J = 15.6 Hz, 1 H), 6.96 (d, J = 8.8 Hz, 2 H), 3.88 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 190.6, 161.6, 144.7, 138.3, 132.6, 130.2, 128.5, 128.4, 127.4, 119.6, 114.3, 55.4.

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