ArticleAngewandte Chemie (International ed. in English)2014
Chemo- and regioselective C(sp³)-H arylation of unactivated allylarenes by deprotonative cross-coupling.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 46 citations in OpenAlex.
- Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis.Natural products and bioprospecting · 2022Review
- Aryl acrylonitriles synthesis enabled by palladium-catalyzed α-alkenylation of arylacetonitriles with vinyl halides/triflates.Frontiers in chemistry · 2022Article
- Article
- Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry.ChemSusChem · 2019Review
- Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts.Journal of the American Chemical Society · 2018Article
- One-pot aminobenzylation of aldehydes with toluenes.Nature communications · 2018Article
- Palladium-Catalyzed Triarylation of spAdvanced synthesis & catalysis · 2018Article
- Synthesis of Diarylated 4-Pyridylmethyl Ethers via Palladium-Catalyzed Cross-Coupling Reactions.Advanced synthesis & catalysis · 2017Article
- Palladium-catalysed synthesis of triaryl(heteroaryl)methanes.Nature communications · 2017Article
- Tandem C(spAdvanced synthesis & catalysis · 2016Article
- Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols.Organic letters · 2016Article
- Positional Selectivity in C-H Functionalizations of 2-Benzylfurans with Bimetallic Catalysts.Journal of the American Chemical Society · 2016Article
- Palladium-Catalyzed C-H Arylation of α,β-Unsaturated Imines: Catalyst-Controlled Synthesis of Enamine and Allylic Amine Derivatives.Angewandte Chemie (International ed. in English) · 2016Article
- Chemoselective Palladium-Catalyzed Deprotonative Arylation/[1,2]-Wittig Rearrangement of Pyridylmethyl Ethers.Chemical science · 2016Article
- Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.Organic letters · 2015Article
- Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(spChemical science · 2015Article
- Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.Advanced synthesis & catalysis · 2014Article
- Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.Chemical communications (Cambridge, England) · 2014Article
- NiXantphos: a deprotonatable ligand for room-temperature palladium-catalyzed cross-couplings of aryl chlorides.Journal of the American Chemical Society · 2014Article
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Authors and funding
4 authors at 3 institutions in 2 countries.
Funding
Abstract
The combination of aryl bromides, allylbenzene, base and a palladium catalyst usually results in a Heck reaction. Herein we combine these same reagents, but override the Heck pathway by employing a strong base. In the presence of LiN(SiMe3)2, allylbenzene derivatives undergo reversible deprotonation. Transmetalation of the resulting allyllithium intermediate to LPdAr(Br) and reductive elimination provide the 1,1-diarylprop-2-enes, which are not accessible by the Heck reaction. The regioselectivity in this deprotonative cross-coupling process is catalyst-controlled and very high.
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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.