ArticleNature communications2022
Highly selective synthesis of all-carbon tetrasubstituted alkenes by deoxygenative alkenylation of carboxylic acids.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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11 citing papers in PubMed, 128 citations in OpenAlex.
- Asymmetric cyanoesterification of vinylarenes by electrochemical copper catalysis.Nature communications · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Stereoselective benzylic C(spChemical science · 2024Article
- Unimolecular Fragment Coupling: A New Bond-Forming Methodology via the Deletion of Atom(s).JACS Au · 2024Review
- Remote-carbonyl-directed sequential Heck/isomerization/C(spNature communications · 2024Article
- Structurally Diverse Bench-Stable Nickel(0) Pre-Catalysts: A Practical Toolkit for In Situ Ligation Protocols.Angewandte Chemie (International ed. in English) · 2023Article
- Photoredox-Mediated Deoxygenative Radical Additions of Aromatic Acids to Vinyl Boronic Esters and gem-Diborylalkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade.Communications chemistry · 2022Article
- Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Highly selective single and multiple deuteration of unactivated C(spNature communications · 2022Article
- Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-onesFrontiers in chemistry · 2022Article
Corrections and comments
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Authors and funding
6 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The synthesis of all-carbon tetrasubstituted olefins under mild reaction conditions is challenging because of the inevitable issues including significant steric hindrance and the uncontrolled Z/E stereoselectivity. In this paper, we report the synthesis of all-carbon tetrasubstituted alkenes from readily available carboxylic acids and alkenyl triflates with the synergistic catalysis of cyclo-octa-1,5-diene(tetramethyl-1,4-benzoquinone)nickel and visible light under an air atmosphere, thus avoiding the need for a glovebox or a Schlenk line. A wide range of aromatic carboxylic acids and cyclic and acyclic alkenyl triflates undergo the C-C coupling process smoothly, forming structurally diverse alkenes stereospecifically in moderate to good yields. The practicality of the method is further illustrated by the late-stage modification of complex molecules, the one pot synthesis and gram-scale applications. This is an important step towards the valuable utilization of carboxylic acids, and it also simplifies the experimental operation of metallophotoredox catalysis with moisture sensitive nickel(0) catalysis.
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