Theoretical Insight into C(sp3)–F Bond Activations and Origins of Chemo- and Regioselectivities of “Tunable” Nickel-Mediated/-Catalyzed Couplings of 2-Trifluoromethyl-1-alkenes with Alkynes
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DOI: 10.1021/acs.organomet.7b00514
Abstract: The mechanisms and chemo- and regioselectivities of divergent (Ni(cod)2/PCy3)-mediated/-catalyzed C(sp3)–F bond activation of 2-trifluoromethyl-1-alkenes (1) with alkynes (2) were investigated by density functional theory (DFT) calculations. The nickel-mediated/-catalyzed reaction involves sequential ligand exchange, alkene coordination,… read more here.
Keywords: chemo regioselectivities; trifluoromethyl alkenes; nickel mediated; mediated catalyzed ... See more keywords
1,2-Dicarbofunctionalization of Trifluoromethyl Alkenes with Pyridinium Salts via a Cycloaddition/Visible-Light-Enabled Fragmentation Cascade.
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DOI: 10.1021/acs.orglett.1c04148
Abstract: Although trifluoromethyl alkenes have great synthetic potential, their 1,2-difunctionalization has been a challenge. In this Letter, we disclose the first 1,2-dicarbofunctionalization of trifluoromethyl alkenes with pyridinium salts via a cascade process involving a base-promoted [3… read more here.
Keywords: salts via; dicarbofunctionalization trifluoromethyl; pyridinium salts; visible light ... See more keywords
Photoredox-Catalyzed Allylic Defluorinative Alkoxycarbonylation of Trifluoromethyl Alkenes through Intermolecular Alkoxycarbonyl Radical Addition.
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DOI: 10.1021/acs.orglett.1c04359
Abstract: The gem-difluoroalkene moiety is an ideal carbonyl bioisostere in medicinal chemistry, but efficient synthesis of β-gem-difluoroalkene esters remains challenging so far. Herein, we disclose a photoredox-catalyzed allylic defluorinative alkoxycarbonylation of trifluoromethyl alkenes enabled by intermolecular… read more here.
Keywords: allylic defluorinative; defluorinative alkoxycarbonylation; alkoxycarbonylation trifluoromethyl; catalyzed allylic ... See more keywords
Photocatalytic Defluorinative Three-Component Reaction of α-Trifluoromethyl Alkenes, Alkenes, and Sodium Sulfinates: Synthesis of Monofluorocyclopentenes.
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DOI: 10.1021/acs.orglett.2c02202
Abstract: A photocatalytic three-component reaction of α-trifluoromethyl alkenes, electron-rich alkenes, and sodium sulfinates for the synthesis of gem-difluoroalkenes in a radical/polar crossover manner was developed. Due to the strong electron-withdrawing nature of the sulfonyl group, the… read more here.
Keywords: trifluoromethyl alkenes; sodium sulfinates; component reaction; three component ... See more keywords
Synthesis of CF3-Substituted Alkylamines, 1,2-Bisazoles, and 1,4,5,6-Tetrahydro-1,2,4-triazines from Newly Designed Tetrazole-Activated Trifluoromethyl Alkenes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03900
Abstract: A new class of Michael acceptor, tetrazolyl-trifluoromethyl alkenes, has been discovered. They readily undergo Michael-type addition instead of addition-elimination reaction with aliphatic amines and azoles to furnish β-trifluoromethyl alkylamines and CF3-substituted 1,2-bisazole derivatives, respectively. Additionally,… read more here.
Keywords: trifluoromethyl; cf3 substituted; tetrahydro triazines; synthesis cf3 ... See more keywords
Dual Roles of TBHP-Enabled Regioselective Hydroetherification of (Trifluoromethyl)alkenes with Boronic Acids: Access to α-Trifluoromethyl β-Aryloxy Tertiary Alcohols
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DOI: 10.1055/a-1481-2023
Abstract: The three-starting materials four-component reaction of (trifluoromethyl)alkenes, TBHP, and boronic acids is reported, delivering various useful α-trifluoromethyl-β-aryloxy tertiary alcohols in high yields and in an exclusively regioselective hydroetherification manner. TBHP serves as both the oxidant… read more here.
Keywords: trifluoromethyl aryloxy; trifluoromethyl alkenes; tertiary alcohols; trifluoromethyl ... See more keywords
Ligand-Free Nickel-Catalyzed Reductive Allylic Defluorinative Cross-Coupling of α-Trifluoromethyl Alkenes with Epoxides
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DOI: 10.1055/s-0040-1707170
Abstract: We report a reductive allylic defluorinative reaction of α-trifluoromethyl alkenes with terminal epoxides, which consists of an iodide-mediated regioselective ring opening and a nickel-catalyzed radical-type cross-coupling, providing diverse tertiary gem-difluorobishomoallylic alcohols in moderate to high… read more here.
Keywords: trifluoromethyl alkenes; allylic defluorinative; reductive allylic; nickel catalyzed ... See more keywords