ArticleJournal of the American Chemical Society2018
A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission.
Article in Journal of the American Chemical Society, 2018. 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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Who cites it
11 citing papers in PubMed, 46 citations in OpenAlex.
- Thermal [2+2] cycloaddition as a route to gem-difluoro heterobicyclo[n.1.1]alkanes.Nature chemistry · 2026Article
- Ligand-controlled divergent enantioselective hydroarylation of cyclobutenes.Chemical science · 2025Article
- Review
- Strain-Inducing Positional Alkene Isomerization.Journal of the American Chemical Society · 2023Article
- Catalytic Dienylation: An Emergent Strategy for the Stereoselective Construction of Conjugated Dienes and Polyenes.Synthesis · 2023Article
- Pd(ii)-catalyzed β- and γ-C-(spChemical science · 2023Article
- Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.Organic process research & development · 2022Review
- Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.Molecules (Basel, Switzerland) · 2021Review
- Dienedioic acid as a useful diene building block via directed Heck-decarboxylate coupling.Communications chemistry · 2020Article
- Highly Stereoselective and Catalytic Desulfitative C-O and C-I Dienylation with Sulfolenes: the Importance of Basic Additives.Tetrahedron · 2019Article
- Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes.Journal of the American Chemical Society · 2019Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Substituted 1,3-dienes are valuable synthetic intermediates used in myriad catalytic transformations, yet modern catalytic methods for their preparation in a highly modular fashion using simple precursors are relatively few. We report here an aerobic boron Heck reaction with cyclobutene that forms exclusively linear 1-aryl-1,3-dienes using (hetero)arylboronic acids, or 1,3,5-trienes using alkenylboronic acids, rather than typical Heck products (i.e., substituted cyclobutenes). Experimental and computational mechanistic data support a pericyclic mechanism for C-C bond cleavage that enables the cycloalkene to circumvent established limitations associated with diene reagents in Heck-type reactions.
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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.