ArticleNature chemistry2019
Carbopalladation of C-C σ-bonds enabled by strained boronate complexes.
Article in Nature chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 70 papers.
What it found
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Who cites it
70 citing papers in PubMed, 224 citations in OpenAlex.
- Borylcyclopropanes: Synthetic Strategies and Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Electrochemical synthesis of 2-oxa-bicyclo[2.1.1]hexanes by anodic oxidation-cyclization relay strategy.Chemical science · 2026Article
- Harnessing Molecular Strain to Program 1,2-Migration in Boronic Ester Chemistry.Chemistry, an Asian journal · 2026Review
- Triplet Energy Transfer-Driven Intermolecular [2+2] Photocycloaddition of Acyclic Imines and Indoles: Facile Access to Azetidine-Fused Indolines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Catalytic asymmetric functionalization of bicyclo[1.1.0]butane boronic esters enabled by 1,2-oxygen migration.Nature communications · 2026Article
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- Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes.Nature communications · 2025Article
- Regiodivergent hydrophosphination of Bicyclo[1.1.0]-Butanes under catalyst control.Nature communications · 2025Article
- Borylated strain rings synthesis via photorearrangements enabled by energy transfer catalysis.Nature communications · 2025Article
- Generation and Use of Bicyclo[1.1.0]butyllithium under Continuous Flow Conditions.Organic letters · 2025Article
- Illuminating Palladium Catalysis.Accounts of chemical research · 2025Article
- Facile Synthesis of Housanes by an Unexpected Strategy.Journal of the American Chemical Society · 2025Article
- Strain-release trifluoromethoxylation and pentafluorosulfanoxylation of [1.1.0]bicyclobutanes: expanded access to fluorinated cyclobutane hybrid bioisosteres.Chemical communications (Cambridge, England) · 2025Article
- Understanding the origin of stereoselectivity in the photochemical denitrogenation of 2,3-diazabicyclo[2.2.1]heptene and its derivatives with non-adiabatic molecular dynamics.Beilstein journal of organic chemistry · 2025Article
- Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C-C cleavage and ruthenium-catalysed remote C-H activation.Nature synthesis · 2025Article
- Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes.Nature communications · 2024Article
- Lewis acid-catalyzed diastereoselective formal ene reaction of thioindolinones/thiolactams with bicyclobutanes.Chemical science · 2024Article
- Article
- Stereoselective polar radical crossover for the functionalization of strained-ring systems.Communications chemistry · 2024Article
10 more citing papers are in PubMed but not listed here.
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
Abstract
Transition-metal-catalysed cross-coupling reactions, particularly those mediated by palladium, are some of the most broadly used chemical transformations. The fundamental reaction steps of such cross-couplings typically include oxidative addition, transmetallation, carbopalladation of a π-bond and/or reductive elimination. Herein, we describe an unprecedented fundamental reaction step: a C-C σ-bond carbopalladation. Specifically, an aryl palladium(II) complex interacts with a σ-bond of a strained bicyclo[1.1.0]butyl boronate complex to enable addition of the aryl palladium(II) species and an organoboronic ester substituent across a C-C σ-bond. The overall process couples readily available aryl triflates and organoboronic esters across a cyclobutane unit with total diastereocontrol. The pharmaceutically relevant 1,1,3-trisubstituted cyclobutane products are decorated with an array of modular building blocks, including a boronic ester that can be readily derivatized.
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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.