ArticleNature chemistry2016
Iterative reactions of transient boronic acids enable sequential C-C bond formation.
Article in Nature chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Tech-Enhanced Synthesis: Exploring the Synergy between Organic Chemistry and Technology.Journal of the American Chemical Society · 2025Review
- Synthesis of Secondary Boronates via Deaminative Cross-Coupling of Alkyl Nitroso Carbamates and Boronic Acids.Angewandte Chemie (International ed. in English) · 2024Article
- Mechanism of Asymmetric Homologation of Alkenylboronic Acids with CFThe Journal of organic chemistry · 2024Article
- Synthesis of substituted benzylboronates by light promoted homologation of boronic acids withChemical science · 2023Article
- Asymmetric Organocatalytic Homologation: Access to Diverse Chiral Trifluoromethyl Organoboron Species.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Bakuchiol - a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches.RSC advances · 2022Review
- Construction of NH-Unprotected Spiropyrrolidines and Spiroisoindolines by [4+1] Cyclizations of γ-Azidoboronic Acids with Cyclic N-Sulfonylhydrazones.Angewandte Chemie (International ed. in English) · 2022Article
- Uncommon carbene insertion reactions.Chemical science · 2021Review
- Preparation of Functionalized Aryl, Heteroaryl, and Benzylic Potassium Organometallics Using Potassium Diisopropylamide in Continuous Flow.Angewandte Chemie (International ed. in English) · 2020Article
- Article
- Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.Nature communications · 2019Article
- Unlocking a Diazirine Long-Lived Nuclear Singlet State via Photochemistry: NMR Detection and Lifetime of an Unstabilized Diazo-Compound.Journal of the American Chemical Society · 2018Article
- Expanding the medicinal chemistry synthetic toolbox.Nature reviews. Drug discovery · 2018Review
- Article
- A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions.Angewandte Chemie (International ed. in English) · 2017Article
- Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids.Chemical science · 2017Article
- An autonomous organic reaction search engine for chemical reactivity.Nature communications · 2017Article
- Probing intermediates of the induction period prior to nucleation and growth of semiconductor quantum dots.Nature communications · 2017Article
- Semibatch monomer addition as a general method to tune and enhance the mechanics of polymer networks via loop-defect control.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.Angewandte Chemie (International ed. in English) · 2017Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C-C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic boronic acids, obtained by reacting flow-generated diazo compounds with boronic acids, and their application in controlled iterative C-C bond forming reactions is described. Thus far we have shown the formation of up to three C-C bonds in a sequence including the final trapping of a reactive boronic acid species with an aldehyde to generate a range of new chemical structures.
Identifiers
27001732What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.