ArticleJournal of the American Chemical Society2016
Design, Synthesis, and Validation of an Effective, Reusable Silicon-Based Transfer Agent for Room-Temperature Pd-Catalyzed Cross-Coupling Reactions of Aryl and Heteroaryl Chlorides with Readily Available Aryl Lithium Reagents.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Catalytic Hydrodechlorination of 4-Chlorophenol by Palladium-Based Catalyst Supported on Alumina and Graphene Materials.Nanomaterials (Basel, Switzerland) · 2023Article
- The 2-Pyridyl Problem: Challenging Nucleophiles in Cross-Coupling Arylations.Angewandte Chemie (International ed. in English) · 2021Review
- The role of CuI in the siloxane-mediated Pd-catalyzed cross-coupling reactions of aryl iodides with aryl lithium reagents.Chinese chemical letters = Zhongguo hua xue kuai bao · 2021Article
- Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.Accounts of chemical research · 2020Review
- Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.The Journal of organic chemistry · 2018Article
- Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution.The Journal of antibiotics · 2018Review
- Design, Synthesis, and Application of Polymer-Supported Silicon-Transfer Agents for Cross-Coupling Reactions with Organolithium Reagents.The Journal of organic chemistry · 2017Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
A reusable silicon-based transfer agent (1) has been designed, synthesized, and validated for effective room-temperature palladium-catalyzed cross-coupling reactions (CCRs) of aryl and heteroaryl chlorides with readily accessible aryl lithium reagents. The crystalline, bench-stable siloxane transfer agent (1) is easily prepared via a one-step protocol. Importantly, this "green" CCR protocol circumvents prefunctionalization, isolation of organometallic cross-coupling partners, and/or stoichiometric waste aside from LiCl. DFT calculations support a σ-bond metathesis mechanism during transmetalation and lead to insights on the importance of the CF3 groups.
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Registered trials
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