Fluorinated Boronic Acids: Acidity and Hydrolytic Stability of Fluorinated Phenylboronic Acids
Sign Up to like & getrecommendations! Published in 2017 at "European Journal of Inorganic Chemistry"
DOI: 10.1002/ejic.201700546
Abstract: Acidity constants and hydrolytic stability of all isomers of fluoro-substituted phenylboronic acids (F1-F5) have been determined by both spectrophotometric and potentiometric methods. Introduction of fluorine into aromatic ring enhances Lewis acidity of boronic acids, depending… read more here.
Keywords: boronic acids; phenylboronic acids; fluorinated boronic; acidity ... See more keywords
Synthesis of Phenyl Dithiocarbamates Starting from Sodium Dialkyldithiocarbamates and Aryl Boronic Acids: a Copper Catalyzed S -Arylation
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DOI: 10.1002/ejoc.201801271
Abstract: A convenient and efficient protocol for the S-arylation of sodium dialkyldithiocarbamates was developed. With the catalysis of copper(I) bromide, sodium dialkyldithiocarbamates coupled with aryl boronic acids giving the C-S coupling products smoothly in good to… read more here.
Keywords: boronic acids; copper; sodium; arylation ... See more keywords
Origins, and formulation implications, of the pKa difference between boronic acids and their esters: A density functional theory study
Sign Up to like & getrecommendations! Published in 2018 at "European Journal of Pharmaceutical Sciences"
DOI: 10.1016/j.ejps.2018.08.017
Abstract: ABSTRACT The purpose of this study is to try to identify the etiology and formulation implications of the significant pKa drop in aqueous solution that occurs when boronic acids are reversibly esterified by reaction with… read more here.
Keywords: density functional; boronic acids; formulation implications; functional theory ... See more keywords
Copper-mediated oxidative pentafluoroethylthiolation of aryl boronic acids with TMSC2F5 and elemental sulfur
Sign Up to like & getrecommendations! Published in 2017 at "Journal of Fluorine Chemistry"
DOI: 10.1016/j.jfluchem.2017.07.008
Abstract: Abstract A copper-mediated oxidative pentafluoroethylthiolation of aryl boronic acids with TMSC 2 F 5 and S 8 was developed. This reaction provides a new access to various aryl pentafluoroethyl thioethers. The use of 2-fluoropyridine as… read more here.
Keywords: boronic acids; mediated oxidative; copper mediated; pentafluoroethylthiolation aryl ... See more keywords
Palladium-Catalyzed Addition/Cyclization of (2-Hydroxyaryl)boronic Acids with Alkynylphosphonates: Access to Phosphacoumarins.
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DOI: 10.1021/acs.orglett.0c03151
Abstract: A facile palladium-catalyzed addition/cyclization of (2-hydroxyaryl)boronic acids with alkynylphosphonates has been developed, providing an effective strategy to construct a series of valuable phosphacoumarins. This methodology features excellent regioselectivity and broad substrate tolerance. read more here.
Keywords: cyclization hydroxyaryl; boronic acids; catalyzed addition; palladium catalyzed ... See more keywords
Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator.
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DOI: 10.1021/acs.orglett.1c00399
Abstract: Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the… read more here.
Keywords: mediated alkenylation; boronic acids; light mediated; visible light ... See more keywords
Regioselective Cross-Coupling of Isatogens with Boronic Acids to Construct 2,2-Disubstituted Indolin-3-one Derivatives.
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DOI: 10.1021/acs.orglett.1c02808
Abstract: Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron "ate" complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with… read more here.
Keywords: boronic acids; one derivatives; disubstituted indolin; indolin one ... See more keywords
Electrochemical Mn-Promoted Radical Selenylation of Boronic Acids with Diselenide Reagents.
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DOI: 10.1021/acs.orglett.2c00607
Abstract: A powerful and environmentally friendly electrochemical manganese-promoted free radical selenylation reaction between boronic acids and diselenide reagents was established. This electrochemical protocol provides a practically applicable way to a series of valuable organoselenium compounds with… read more here.
Keywords: boronic acids; acids diselenide; electrochemical promoted; diselenide reagents ... See more keywords
Rhodium(I)-Catalyzed Defluorinative Coupling of Boronic Acids with Monofluoroalkenes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02294
Abstract: We herein describe a highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-β-monofluoroacrylates. In contrast to previous methods, the trisubstituted (Z)-alkene products were obtained in excellent dr with an inversion of double bond geometry.… read more here.
Keywords: boronic acids; catalyzed defluorinative; defluorinative coupling; coupling boronic ... See more keywords
Combinatorial Nickel-Catalyzed Monofluoroalkylation of Aryl Boronic Acids with Unactivated Fluoroalkyl Iodides.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.7b02012
Abstract: A combinatorial nickel-catalyzed cross-coupling between arylboronic acids and unactived 1-fluoro-1-iodoalkanes has been developed, which demonstrated high efficiency, mild conditions, and excellent functional-group compatibility. Readily available nitrogen and phosphine ligands were combined with a nitrogen source,… read more here.
Keywords: monofluoroalkylation aryl; boronic acids; aryl boronic; combinatorial nickel ... See more keywords
Transition-Metal-Free Stereocomplementary Cross-Coupling of Diols with Boronic Acids as Nucleophiles.
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DOI: 10.1021/acs.orglett.7b03192
Abstract: The transition-metal-free diastereoselective C(sp2)-C(sp3) cross-coupling between unprotected diols and boronic acids or potassium organotrifluoroborates is reported. Depending on the reaction conditions, the syn or the anti reaction products are obtained in a stereocomplementary fashion. This… read more here.
Keywords: boronic acids; transition metal; diols boronic; metal free ... See more keywords