Synlett, Table of Contents

Synlett 2023; 34(11): 1280-1284
DOI: 10.1055/a-2007-2958

letter

Ligand-Free Palladium-Catalyzed Substoichiometric Base Mediated Carbonylation of Aryl Iodides with Alkenylboronic Acids under Ambient Conditions

Lili Tang‡

^aHunan Engineering Research Center for Recycled Aluminum, College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China

,

Yanqun Gao‡

^bJiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional 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

^bJiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional 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

,

Linlin Yang

^bJiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional 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

,

Bing Xiao

^bJiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional 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

,

Ge Shen

^bJiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional 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

,

Yuejun Ouyang∗

^aHunan Engineering Research Center for Recycled Aluminum, College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China

,

Wei Han ∗

^bJiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional 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

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Abstract

A highly efficient, practical, and ligand-free palladium-catalyzed carbonylation of aryl iodides with alkenylboronic acids has been developed. A variety of chalcones and α-branched enones were isolated in satisfactory to good yields with good substrate compatibilities under an ambient pressure of CO at room temperature. Moreover, the transformation proceeds well in the presence of a substoichiometric amount of base. The merit of this strategy as a late-stage functionalization platform has been demonstrated by modifications of complex substrates derived from estrone and 3-phenyl-l-alanine.

Key words

Key words

palladium catalysis - carbonylation - aryl iodides - alkenylboronic acids - chalcones - enones

References and Notes

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13 (2E)-1-(4-Nitrophenyl)-3-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-iodo-4-nitrobenzene (1a; 0.25 mmol, 62.9 mg), (E)-styrylboronic acid (2a; 0.30 mmol, 45.8 mg), Na₂CO₃ (0.125 mmol, 13.3 mg), PivOH (0.125 mmol, 13.2 mg), and PEG-400 (2.0 g), then subjected to several standard cycles of evacuation and backfilling with pure dry CO. The mixture was then stirred at RT and atmospheric pressure for 3 h. When the reaction was complete, the mixture was extracted with Et₂O (3 × 15 mL). The organic phases were combined, and the volatile components were evaporated under reduced pressure. The crude product was purified by column chromatography [silica gel, PE–Et₂O (100:1 to 10:1)] to give a yellow solid; yield: 59 mg (94%, E/Z > 99:1); mp 143–144 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.37 (d, J = 8.8 Hz, 2 H), 8.17 (d, J = 8.8 Hz, 2 H), 7.88 (d, J = 15.6 Hz, 1 H), 7.69–7.67 (m, 2 H), 7.51 (d, J = 15.6 Hz, 1 H), 7.48–7.45 (m, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 189.0, 150.0, 146.8, 143.0, 134.3, 131.2, 129.4, 129.1, 128.7, 123.8, 121.2.

Supplementary Material

Supplementary Material

Supporting Information