Numerous reactions generating C-Si and C-B bonds are in focus owing to the importance of incorporating silicon or boron into new or existing drugs, in addition to their use as building blocks in cross-coupling reactions en route to various targets of both natural and unnatural origins. In this review, recent protocols relying on copper-catalyzed sp carbon-silicon and carbon-boron bond-forming reactions are discussed.
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http://dx.doi.org/10.3762/bjoc.16.67 | DOI Listing |
J Org Chem
January 2025
Institute of Organic Chemistry, RWTH Aachen University, 52074 Aachen, Germany.
In contrast to what one can be led to believe upon inspecting some of the recent literature, the dehydrogenative phenothiazination reaction does not require onerous technologies, complicated setups, or advanced catalysts in order to be mild and sustainable. We demonstrate this herein with a most facile, cost-effective, and sustainable Cu(II) catalyzed method, under 1 atm of O at room temperature in methanol, providing broad scope and high yields. These new results further set the dehydrogenative phenothiazination reaction among the green and practical coupling concepts of chemistry.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, Pennsylvania, 15213, United States.
Photomediated Atom Transfer Radical Polymerization (photoATRP) is an activator regeneration method, which allows for the controlled synthesis of well-defined polymers via light irradiation. Traditional photoATRP is often limited by the need for high-energy ultraviolet or violet light. These could negatively affect the control and selectivity of the polymerization, promote side reactions, and may not be applicable to biologically relevant systems.
View Article and Find Full Text PDFOrg Lett
December 2024
Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Calle Francisco Tomás y Valiente 7, 28049 Madrid, Spain.
Cyclic peptides are valued synthetic targets in organic and medicinal chemistry. Herein, we report an efficient strategy for the synthesis of unnatural cyclic peptides via the Cu-catalyzed 1,3-dipolar cycloaddition of azomethylene ylides. Linear precursors of different lengths and bearing diverse amino acids (26 examples) are shown to be compatible with this method, affording good yields and complete -diastereoselectivities.
View Article and Find Full Text PDFJ Am Chem Soc
November 2024
Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 200240, China.
Nucleoside analogues have seen significant advancements in treating viral infections and cancer through ProTide technology, leading to a series of FDA-approved drugs such as sofosbuvir, tenofovir alafenamide, and remdesivir. The stereochemical configuration at the phosphorus center of ProTides significantly influences their pharmacological properties, necessitating efficient stereoselective synthesis. Traditional methods using chiral auxiliaries or nonracemic phosphorylating agents are labor-intensive and inefficient, while recent organocatalytic approaches, despite their promise, still face limitations.
View Article and Find Full Text PDFChem Sci
September 2024
Florida State University, Department of Chemistry and Biochemistry, Laboratories of Molecular Recognition 95 Chieftan Way Tallahassee FL 32306 USA
This article describes the first enantioselective synthesis of the Tasmanian marine alkaloid (+)-cylindricine B. The concise construction of the compound hinged on dearomative retrosynthetic logic combined with a tactical advance in the generation of congested, cyclic, alpha-tertiary amine centers. The scope of this key coupling reaction was explored in addition to providing a synthetic application for Cu-catalyzed enantioselective dearomatization of -acyl-pyridiniums.
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