Palladium-Catalyzed Stereoselective Hydrodefluorination of Tetrasubstituted gem-Difluoroalkenes.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
DOI: 10.1021/acs.orglett.0c01813
Abstract: A highly stereoselective palladium(0)-catalyzed hydrodefluorination (HDF) of tetrasubstituted gem-difluoroalkenes is developed. By using catalytic Pd(PPh3)4 (2.5-5 mol %) and hydrosilane Me2PhSiH, various trisubstituted terminal (E)-monofluoroalkenes can be synthesized with excellent E/Z selectivity (>99:1) and good… read more here.
Keywords: tetrasubstituted gem; catalyzed stereoselective; gem difluoroalkenes; palladium catalyzed ... See more keywords
Photoredox-Catalyzed Difunctionalization of Unactivated Olefins for Synthesizing Lactam-Substituted gem-Difluoroalkenes.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c03329
Abstract: Herein, the synthesis of lactam-substituted gem-difluoroalkenes has been developed through a photoredox-catalyzed radical cascade reaction. This developed photoredox-catalyzed, Brønsted base-assisted intramolecular 5-exo-trig cyclization/intermolecular radical addition/β-fluoride elimination reaction offers a simple method for producing lactam, carbamate,… read more here.
Keywords: gem difluoroalkenes; photoredox catalyzed; lactam substituted; substituted gem ... See more keywords
Highly Selective C-F Bond Functionalization of Tetrasubstituted gem-Difluoroalkenes and Trisubstituted Monofluoroalkenes Using Grignard Reagents.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01639
Abstract: We herein describe selective C-F bond functionalizations of tetrasubstituted gem-difluoroalkenes and trisubstituted monofluoroalkenes using Grignard reagents without the transition metal catalyst. β,β-Difluoroacrylates react with Grignard reagents under mild conditions to afford tetrasubstituted (E)-β-monofluoroacrylates. Experimental and… read more here.
Keywords: difluoroalkenes trisubstituted; grignard reagents; tetrasubstituted gem; gem difluoroalkenes ... See more keywords
Visible-Light-Induced C-F and C-N Bond Cleavage for the Synthesis of gem-Difluoroalkenes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02528
Abstract: Herein, we describe a novel and efficient photoredox catalytic radical addition/defluoroalkylation coupling reaction between primary amines and trifluoromethyl-substituted alkenes. A series of gem-difluoroalkenes were synthesized via C-N bond cleavage of α-3°, α-2°, and α-1° amines… read more here.
Keywords: gem difluoroalkenes; bond cleavage; visible light;
Copper-Catalyzed Hydroamination of gem-Difluoroalkenes Access to Diversified α-Difluoromethyl Amines.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.2c04278
Abstract: The difluoromethyl group (CF2H) is of great importance in medicinal chemistry. We report herein an efficient method for the synthesis of diversified α-difluoromethyl amines through copper-catalyzed hydroamination of gem-difluoroalkenes, where the C-N bond formed via… read more here.
Keywords: gem; gem difluoroalkenes; catalyzed hydroamination; difluoromethyl amines ... See more keywords
Chromium-Catalyzed Defluorinative Reductive Coupling of Aldehydes with gem-Difluoroalkenes.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c00016
Abstract: Herein, a mild and convenient defluorinative reductive cross coupling of gem-difluoroalkenes with aliphatic aldehydes has been developed to afford diverse silyl-protected β-fluorinated allylic alcohols. The reaction is operationally simple and shows good functional group tolerance… read more here.
Keywords: catalyzed defluorinative; defluorinative reductive; gem difluoroalkenes; reductive coupling ... See more keywords
Electrochemical Difunctionalization of gem-Difluoroalkenes: A Metal-Free Synthesis of α-Difluoro(alkoxyl/azolated) Methylated Ethers.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01130
Abstract: A scalable electrochemical difunctionalization of gem-difluoroalkenes to structurally versatile difluoro motifs was achieved. This methodology features reagent-free conditions, good functional group tolerance, and a relatively broad substrate scope. Meanwhile, the electrolysis protocol is easy to… read more here.
Keywords: difunctionalization gem; gem difluoroalkenes; difluoro; electrochemical difunctionalization ... See more keywords
Cu-Catalyzed Stereoselective Borylation of gem-Difluoroalkenes with B2pin2.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.7b01430
Abstract: A novel and efficient method for the synthesis of (Z)-fluorinated alkenylboronic acid pinacol esters via Cu-catalyzed stereoselective borylation of gem-difluoroalkenes using bis(pinacolato)diboron (B2pin2) as the boron source with the assistance of NaOtBu and Xantphos at… read more here.
Keywords: gem difluoroalkenes; borylation gem; catalyzed stereoselective; stereoselective borylation ... See more keywords
Zinc-Mediated Decarboxylative Alkylation of Gem-difluoroalkenes.
Sign Up to like & getrecommendations! Published in 2018 at "Organic letters"
DOI: 10.1021/acs.orglett.8b01866
Abstract: An efficient and mild zinc-mediated decarboxylative alkylation of gem-difluoroalkenes with N-hydroxyphthalimide (NHP) esters, to give monofluoroalkenes in moderate to excellent yields with high Z-selectivity is reported. The reaction tolerates a broad range of functional groups… read more here.
Keywords: mediated decarboxylative; decarboxylative alkylation; gem difluoroalkenes; alkylation gem ... See more keywords
Alkyltriflones in the Ramberg-Bäcklund Reaction: An Efficient and Modular Synthesis of gem-Difluoroalkenes.
Sign Up to like & getrecommendations! Published in 2020 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.0c07924
Abstract: The unprecedented synthesis of gem-difluoroalkenes through the Ramberg-Bäcklund reaction of alkyl triflones is described herein. Structurally diverse, fully-substituted gem-difluoroalkenes that are difficult to prepare by other methods can be easily prepared from readily available triflones… read more here.
Keywords: gem; gem difluoroalkenes; cklund reaction; synthesis gem ... See more keywords
Advances in silylation and borylation of fluoroarenes and gem-difluoroalkenes via C-F bond cleavage.
Sign Up to like & getrecommendations! Published in 2021 at "Chemical communications"
DOI: 10.1039/d1cc04729a
Abstract: Organoboron and organosilane compounds are widely used in organic synthesis and pharmaceuticals. In addition, the C-F bond functionalization is a useful tool for the construction of carbon-carbon and carbon-heteroatom bonds. In particular, the late-stage functionalization… read more here.
Keywords: borylation fluoroarenes; bond; advances silylation; fluoroarenes gem ... See more keywords