ArticleJournal of the American Chemical Society2021
A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 63 citations in OpenAlex.
- Stick to the beads: supercharging medicinal chemistry and methodology development with ChemBeads.RSC medicinal chemistry · 2026Review
- Late-Stage Cross-Electrophile Coupling of Arylthianthrenium Salts with (Hetero)aryl (Pseudo)halides via Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Selective Ni-Catalyzed Cross-Electrophile Coupling of Heteroaryl Chlorides and Aryl Bromides at 1:1 Substrate Ratio.Journal of the American Chemical Society · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- An Air-Stable, Single-Component Iridium Precatalyst for the Borylation of C-H Bonds on Large to Miniaturized Scales.Journal of the American Chemical Society · 2024Article
- Kinetics and Mechanism of PPhJournal of the American Chemical Society · 2024Article
- Nickel-Catalyzed Atroposelective Cross-Electrophile Coupling of Aryl Halides: A General and Practical Route to Diverse MOP-Type Ligands.Journal of the American Chemical Society · 2024Article
- Development of a selective and scalableRSC advances · 2024Article
- Deep Electroreductive Chemistry: Harnessing Carbon- and Silicon-based Reactive Intermediates in Organic Synthesis.ACS catalysis · 2023Article
- Readily Accessible High-Throughput Experimentation: A General Protocol for the Preparation of ChemBeads and EnzyBeads.ACS medicinal chemistry letters · 2023Article
- Multimetallic-Catalyzed C-C Bond-Forming Reactions: From Serendipity to Strategy.Journal of the American Chemical Society · 2023Review
- A Brief Introduction to Chemical Reaction Optimization.Chemical reviews · 2023Review
- Ni- and Ni/Pd-Catalyzed Reductive Coupling of Lignin-Derived Aromatics to Access Biobased Plasticizers.ACS central science · 2023Article
- Control of Redox-Active Ester Reactivity Enables a General Cross-Electrophile Approach to Access Arylated Strained Rings.Angewandte Chemie (International ed. in English) · 2022Article
- Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.The Journal of organic chemistry · 2022Review
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
Despite their importance to medicine and materials science, the synthesis of biheteroaryls by cross-coupling remains challenging. We describe here a new, general approach to biheteroaryls: the Ni- and Pd-catalyzed multimetallic cross-Ullmann coupling of heteroaryl halides with triflates. An array of 5-membered, 6-membered, and fused heteroaryl bromides and chlorides, as well as aryl triflates derived from heterocyclic phenols, proved to be viable substrates in this reaction (62 examples, 63 ± 17% average yield). The generality of this approach to biheteroaryls was further demonstrated in 96-well plate format at 10 μmol scale. An array of 96 possible products provided >90% hit rate under a single set of conditions. Further, low-yielding combinations could be rapidly optimized with a single "Toolbox Plate" of ligands, additives, and reductants.
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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.