Recent advances in Cu-catalyzed C(sp)-Si and C(sp)-B bond formation.

Beilstein J Org Chem

Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, USA.

Published: April 2020

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.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7176932PMC
http://dx.doi.org/10.3762/bjoc.16.67DOI Listing

Publication Analysis

Top Keywords

advances cu-catalyzed
4
cu-catalyzed csp-si
4
csp-si csp-b
4
csp-b bond
4
bond formation
4
formation numerous
4
numerous reactions
4
reactions generating
4
generating c-si
4
c-si c-b
4

Similar Publications

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 PDF

Better Together: Photoredox/Copper Dual Catalysis in Atom Transfer Radical Polymerization.

Angew 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 PDF

Unnatural Cyclopeptide Synthesis via Cu-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides.

Org 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 PDF

Ligand-Enabled Cu-Catalyzed Stereoselective Synthesis of P-Stereogenic ProTides.

J 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 PDF

Enantioselective total synthesis of (+)-cylindricine B.

Chem 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.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!