ArticleNature chemistry2022
Reversible C-C bond formation using palladium catalysis.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 43 citations in OpenAlex.
- Substrate-Controlled Enantiodivergence in Ni-Catalyzed Access to Phosphorylated Oxindoles With Quaternary Stereocenters.Angewandte Chemie (International ed. in English) · 2026Article
- (Poly)Borylated Species as Modern Reactive Groups toward Unusual Synthetic Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Kharasch-Type Haloalkylation of Alkenes by Photoinduced Copper Catalysis.Journal of the American Chemical Society · 2025Article
- Shuttle HAT for mild alkene transfer hydrofunctionalization.Nature communications · 2024Article
- Palladium/XuPhos-catalyzed enantioselective cascade Heck/intermolecular C(spChemical science · 2024Article
- Nickel-catalyzed switchable arylative/endo-cyclization of 1,6-enynes.Nature communications · 2024Article
- Mechanistic Investigation of the Rhodium-Catalyzed Transfer Hydroarylation Reaction Involving Reversible C-C Bond Activation.Journal of the American Chemical Society · 2023Article
- C(alkyl)-C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction.Nature communications · 2023Article
- Temperature-induced formation of Pd nanoparticles in heterogeneous nanobiohybrids: application in C-H activation catalysis.Nanoscale advances · 2023Article
- Ni-Catalyzed Oxygen Transfer from NJournal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A widely appreciated principle is that all reactions are fundamentally reversible. Observing reversible transition metal-catalysed reactions, particularly those that include the cleavage of C-C bonds, is more challenging. The development of palladium- and nickel-catalysed carboiodination reactions afforded access to the cis and trans diastereomers of the iodo-dihydroisoquinolone products. Using these substrates, an extensive study investigating the reversibility of C-C bond formation using a simple palladium catalyst was undertaken. Herein we report a comprehensive investigation of reversible C-C bond formation using palladium catalysis employing diastereomeric neopentyl iodides as the starting point. It was shown that both diastereomers could be converted to a common product under identical catalytic conditions. A combination of experimental and computational studies were used to probe the operative mechanism. A variety of concepts key to understanding the process of reversible C-C bond formations were investigated, including the effect of electronic and steric parameters on the C-C bond-cleavage step.
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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.