ArticleNature2016
Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis.
Article in Nature, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 52 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
52 citing papers in PubMed.
- Divergent and programmable skeletal remodeling of complex macrocycles with a small method set.Science (New York, N.Y.) · 2026Article
- Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review.Beilstein journal of organic chemistry · 2026Review
- Stereoselective Synthesis of Alkenyl Fluorides and Alkynes by Defluoro Coupling of Trifluoromethyl Arenes.Angewandte Chemie (International ed. in English) · 2025Article
- Applications of Olefin Metathesis in the Synthesis of Fluorinated Substrates and Design of Fluorinated Catalysts.Topics in current chemistry (Cham) · 2025Review
- Stereo-reversed E2 unlocksScience (New York, N.Y.) · 2025Article
- Anti-Markovnikov hydro- and deuterochlorination of unsaturated hydrocarbons using iron photocatalysis.Nature synthesis · 2025Article
- Full on-device manipulation of olefin metathesis for precise manufacturing.Nature nanotechnology · 2025Article
- Preserving precise choreography of bonds in Z-stereoretentive olefin metathesis by using quinoxaline-2,3-dithiolate ligand.Nature communications · 2024Article
- Synthesis ofJournal of the American Chemical Society · 2024Article
- Article
- Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers.Beilstein journal of organic chemistry · 2024Article
- An Anthracene-Thiolate-Ligated Ruthenium Complex: Computational Insights into Z-Stereoselective Cross Metathesis.The journal of physical chemistry. A · 2023Article
- Practical Synthesis of Terminal Vinyl Fluorides.The Journal of organic chemistry · 2023Article
- Photoinduced Chloroamination Cyclization Cascade withThe Journal of organic chemistry · 2023Article
- Copper-Catalyzed Enantioselective Borylative Allyl-Allyl Coupling of Allenes and AllylicACS catalysis · 2023Article
- Article
- Molybdenum(VI) Bis(imido) Complexes: From Frustrated Lewis Pairs to Weakly Coordinating Cations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Cationic molybdenum oxo alkylidenes stabilized by N-heterocyclic carbenes: from molecular systems to efficient supported metathesis catalysts.Chemical science · 2022Article
- Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.Angewandte Chemie (International ed. in English) · 2022Article
- Stereodefined alkenes with a fluoro-chloro terminus as a uniquely enabling compound class.Nature chemistry · 2022Article
Corrections and comments
- Commented on by
Authors and funding
5 authors.
Funding
Abstract
Olefin metathesis has had a large impact on modern organic chemistry, but important shortcomings remain: for example, the lack of efficient processes that can be used to generate acyclic alkenyl halides. Halo-substituted ruthenium carbene complexes decompose rapidly or deliver low activity and/or minimal stereoselectivity, and our understanding of the corresponding high-oxidation-state systems is limited. Here we show that previously unknown halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of a catalyst that is generated in situ and used with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents, and proceed to high conversion at ambient temperature within four hours. We obtain many alkenyl chlorides, bromides and fluorides in up to 91 per cent yield and complete Z selectivity. This method can be used to synthesize biologically active compounds readily and to perform site- and stereoselective fluorination of complex organic molecules.
Indexed as
Identifiers
What 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.