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Electrophilic reagent reductive coupling chemistry
Build complex chemical bonds gently and efficiently to assist in the synthesis of pharmaceutical materials.
Type
Synthesis method
Tags
Other resource gains
Organic synthetic chemistry
An electrophile
Reductive coupling
Metal catalyzed
Solution maturity
Mass promotion / Mass production
Cooperation methods
Joint venture cooperation
Applicable industry
Scientific research and technology services
Applications
Organic synthesis
Key innovations
This technological innovation lies in the efficient and selective construction of complex C-C bonds to overcome the challenges of alkyl systems. Its mild conditions and direct coupling method simplify the synthetic route, reduce reagents and energy consumption, and have important application potential.
Potential economic benefits
This efficient chemical bond construction technology can significantly reduce the production costs of drugs and materials, improve yield and efficiency, reduce resource consumption and environmental impact, and promote the growth of industrial economic benefits.
Potential climate benefits
Efficient chemical bond construction reduces energy consumption, reduces byproducts and waste, avoids harmful reagents, and improves the green level of chemical synthesis.
Solution supplier
View more
Shanghai University
Shanghai University
Shanghai University is a comprehensive research university in Shanghai, committed to cultivating high-quality innovative talents and serving national and regional economic and social development.
Shanghai,China
Solution details

This project is based on a new efficient method of constructing chemical bonds in the chemical field. It has important application value for the synthesis of chemically-related molecules such as drug synthesis chemistry and material synthesis.


Metal-catalyzed coupling chemistry is currently one of the most active directions in the field of organic chemistry. It has become one of the most widely used methods in the academic and industrial fields in the construction of carbon-carbon bonds and carbon-heteroatom bonds. To this end, the 2010 Nobel Prize in Chemistry was awarded to three scientists who have made outstanding contributions in the field of metal-catalyzed coupling chemistry. In general, the most common coupling chemistry is based on the reaction between ldquo; nucleophile rdquo; and ldquo; electrophile rdquo;. Among them, the selection range of ldquo; nucleophiles rdquo; can be traditional organic electron-rich groups such as carbanions (including organometallic nucleophiles R-M), N, O heteroatoms, etc.; it can also be currently popular C-H compounds. The range of ldquo; electrophilic reagents rdquo; is also wider. Generally, compounds whose carbon atom is connected to other atoms or groups that are more electronegative than its electronegative and can undergo nucleophilic substitution reactions on the carbon atom can be considered organic electrophiles.


However, in traditional metal-catalyzed coupling reactions, cross-linking coupling reactions for alkyl electrophilic systems are a more challenging direction than aromatic systems. This is because alkyl electrophiles such as haloalkane R-X are generally not susceptible to oxidative addition

addition), but it is prone to side reactions such as beta;-bit elimination. Therefore, it was not until 2000 that various cross-linking reactions catalyzed by metals (especially Ni and Pd) represented by Professor Fu of MIT actually unfolded in alkyl systems.


The preparation of organometallic nucleophiles generally comes from electrophilic reagent precursors. In order to avoid the difficulty of preparing and storing organometallic nucleophiles, direct coupling reactions based on different electrophiles are attracting attention from the academic community. As one of the first two research groups to intervene in the field of reductive coupling of alkyl electrophiles, our leading contributions and research content in this field are mainly reflected in the following three aspects: (1) For the first time, we achieved an efficient cross-Wurtz reaction method, allowing two different alkanes with similar reactivity to form C(sp3) ndash;C(sp3) bonds under mild conditions, and successfully solved the extremely challenging chemical selectivity problem under a Ni catalyst system;(2) We solved the problem that it was extremely difficult for highly hindered tertiary haloalkanes to participate in the reaction, and achieved a new method of efficient construction of quaternary carbon centers;(3) We developed new reductive coupling methods including ldquo; asymmetric allyl ester/aldehyde addition rdquo;, ldquo; haloalkane acylation, esterification, and arylation reactions rdquo; etc.


At present, nearly 40 academic papers (including 4 J. Am. Chem. Soc., 2 Angew. Chem. Int. Ed. and 1 Chem. Sci.),And is ranked among the Top in famous chemistry journals and book series. Curr. Chem. was invited to publish a review of reductive coupling. At present, he has cited about 800 work in this area, of which 9 papers have been promoted by Synfacts journals, 1 paper has been reported by Synform as a special topic on Synstory, and 2 papers have been included as important organic chemistry progress in organic chemistry, the famous organic chemistry website ldquo; organic-chemistry. orgrdquo;. Among them in Org. Account written by Chem. Front. was selected as the Top 1% highly cited 2017 Royal Society of Chemistry Journal

paper)。


Last updated
07:05:44, Nov 05, 2025
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