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Synlett 2024; 35(12): 1405-1410
DOI: 10.1055/s-0042-1751516
DOI: 10.1055/s-0042-1751516
letter
Iridium-Catalyzed Ligand-Controlled Semi-Reduction of Alkynes Employing H2O as the Hydrogen Donor and Its Application
This work was supported in part by grants from the “333 Project” Scientific Research Project of Jiangsu Province (No. BRA2020204), Research Project of Nantong Health and Health Commission (No. MS2023041), TCM Science and Technology Development Plan of Jiangsu Province (No. MS2021060), Top Six Types of Talents’ Financial Assistance of Jiangsu Province (No. 2019-WSW-199), and Nantong University Clinical Medicine Special Project (Nos. 2022JY003, 2022LY009, 2022HY003).
Abstract
An iridium-catalyzed ligand-controlled semi-reduction of alkynes employing H2O as the hydrogen donor, together with its application, is reported. The use of di-tert-butylphosphinous chloride is crucial for stereoselectivity toward Z-olefins, whereas the use of 2-(diphenylphosphino)benzaldehyde is crucial for stereoselectivity toward E-olefins. More than 35 alkenes were obtained in good yields and high stereoselectivities. The utility of the current method in practical applications was investigated by studying the drug effects of (E)-1,3-dimethoxy-5-styrylbenzene on nerve growth in a zebrafish model.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751516.
- Supporting Information
Publication History
Received: 01 August 2023
Accepted after revision: 25 September 2023
Article published online:
02 November 2023
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- 12 (Z)-Alkenes 2; General Procedure A 15 mL pressure tube was charged with the appropriate alkyne 1 (0.1 mmol) and [Ir(cod)Cl]2 (2.5 μmol, 1.68 mg) under a N2 atmosphere. t-Bu2PCl (0.02 mmol, 3.8 μL), H2O (10 mmol, 180 μL), and THF (1.5 mL) were added, and the resultant mixture was heated at 120 °C with stirring for ~24 h under N2. The solution was then cooled to r.t. and diluted with EtOAc (5 mL). The organic phases were washed with brine, and the aqueous phase was extracted with EtOAc. The organic phases were dried, filtered, and concentrated to give a crude product that was purified by column chromatography [silica gel, hexane or hex–EtOAc (100:1 to 40:1)]. (Z)-1,2-Diphenylethene (2a)13 Colorless liquid; yield: 16.2 mg (90%). 1H NMR (400 MHz, CDCl3): δ = 7.26–7.17 (m, 10 H), 6.60 (d, J = 1.5 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 137.4, 130.4, 129.0, 128.3, 127.2. (E)-Alkenes 3; General Procedure A 15 mL pressure tube was charged with the appropriate alkyne 1 (0.1 mmol) and [Ir(cod)Cl]2 (2.5 μmol, 1.68 mg) under a N2 atmosphere. DPPBde (0.02 mmol, 5.8 mg), H2O (10 mmol, 180 μL), and THF (1.5 mL) were added, and the resultant mixture was heated at 120 °C with stirring for ~28 h under N2; the slightly longer reaction time might be beneficial for the isomerization. The solution was then cooled to r.t. and diluted with EtOAc (5 mL). The organic phases were washed with brine, and the aqueous phase was extracted with EtOAc. The organic phases were dried, filtered, and concentrated to give a crude product that was purified by column chromatography [silica gel, hexane or hex–EtOAc (100:1 to 40:1)]. (E)-1,2-Diphenylethene (3a)13 White solid; yield: 15.6 mg (87%). 1H NMR (400 MHz, CDCl3): δ = 7.52 (d, J = 7.3 Hz, 4 H), 7.36 (t, J = 7.6 Hz, 4 H), 7.26 (dd, J = 10.0, 4.6 Hz, 2 H), 7.11 (s, 2 H). 13C NMR (100 MHz, CDCl3): δ = 137.5, 128.8, 127.8, 126.6.
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