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Steven V. Ley - One of the best experts on this subject based on the ideXlab platform.
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Iterative reactions of transient Boronic Acids enable sequential C–C bond formation
Nature Chemistry, 2016Co-Authors: Claudio Battilocchio, Florian Feist, Andreas Hafner, Meike Simon, Duc N. Tran, Daniel M. Allwood, David C. Blakemore, Steven V. LeyAbstract:The ability to form multiple carbon–carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C–C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C–C bond forming reactions is described. Thus far we have shown the formation of up to three C–C bonds in a sequence including the final trapping of a reactive Boronic acid species with an aldehyde to generate a range of new chemical structures. The ability to form multiple carbon–carbon bonds in a controlled sequence represents an important goal in modern chemical synthesis. Here, the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C–C bond forming reactions is described.
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iterative reactions of transient Boronic Acids enable sequential c c bond formation
Nature Chemistry, 2016Co-Authors: Claudio Battilocchio, Florian Feist, Andreas Hafner, Meike Simon, Duc N. Tran, Daniel M. Allwood, David C. Blakemore, Steven V. LeyAbstract:The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C-C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C-C bond forming reactions is described. Thus far we have shown the formation of up to three C-C bonds in a sequence including the final trapping of a reactive Boronic acid species with an aldehyde to generate a range of new chemical structures.
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metal free coupling of saturated heterocyclic sulfonylhydrazones with Boronic Acids
ChemInform, 2014Co-Authors: Daniel M. Allwood, David C. Blakemore, Alan Daniel Brown, Steven V. LeyAbstract:A procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic sulfonylhydrazones with aryl Boronic Acids is developed.
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metal free coupling of saturated heterocyclic sulfonylhydrazones with Boronic Acids
Journal of Organic Chemistry, 2014Co-Authors: Daniel M. Allwood, David C. Blakemore, Alan Daniel Brown, Steven V. LeyAbstract:The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic Boronic Acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2–sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.
Daniel M. Allwood - One of the best experts on this subject based on the ideXlab platform.
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Iterative reactions of transient Boronic Acids enable sequential C–C bond formation
Nature Chemistry, 2016Co-Authors: Claudio Battilocchio, Florian Feist, Andreas Hafner, Meike Simon, Duc N. Tran, Daniel M. Allwood, David C. Blakemore, Steven V. LeyAbstract:The ability to form multiple carbon–carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C–C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C–C bond forming reactions is described. Thus far we have shown the formation of up to three C–C bonds in a sequence including the final trapping of a reactive Boronic acid species with an aldehyde to generate a range of new chemical structures. The ability to form multiple carbon–carbon bonds in a controlled sequence represents an important goal in modern chemical synthesis. Here, the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C–C bond forming reactions is described.
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iterative reactions of transient Boronic Acids enable sequential c c bond formation
Nature Chemistry, 2016Co-Authors: Claudio Battilocchio, Florian Feist, Andreas Hafner, Meike Simon, Duc N. Tran, Daniel M. Allwood, David C. Blakemore, Steven V. LeyAbstract:The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C-C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C-C bond forming reactions is described. Thus far we have shown the formation of up to three C-C bonds in a sequence including the final trapping of a reactive Boronic acid species with an aldehyde to generate a range of new chemical structures.
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metal free coupling of saturated heterocyclic sulfonylhydrazones with Boronic Acids
ChemInform, 2014Co-Authors: Daniel M. Allwood, David C. Blakemore, Alan Daniel Brown, Steven V. LeyAbstract:A procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic sulfonylhydrazones with aryl Boronic Acids is developed.
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metal free coupling of saturated heterocyclic sulfonylhydrazones with Boronic Acids
Journal of Organic Chemistry, 2014Co-Authors: Daniel M. Allwood, David C. Blakemore, Alan Daniel Brown, Steven V. LeyAbstract:The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic Boronic Acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2–sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.
David C. Blakemore - One of the best experts on this subject based on the ideXlab platform.
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Iterative reactions of transient Boronic Acids enable sequential C–C bond formation
Nature Chemistry, 2016Co-Authors: Claudio Battilocchio, Florian Feist, Andreas Hafner, Meike Simon, Duc N. Tran, Daniel M. Allwood, David C. Blakemore, Steven V. LeyAbstract:The ability to form multiple carbon–carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C–C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C–C bond forming reactions is described. Thus far we have shown the formation of up to three C–C bonds in a sequence including the final trapping of a reactive Boronic acid species with an aldehyde to generate a range of new chemical structures. The ability to form multiple carbon–carbon bonds in a controlled sequence represents an important goal in modern chemical synthesis. Here, the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C–C bond forming reactions is described.
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iterative reactions of transient Boronic Acids enable sequential c c bond formation
Nature Chemistry, 2016Co-Authors: Claudio Battilocchio, Florian Feist, Andreas Hafner, Meike Simon, Duc N. Tran, Daniel M. Allwood, David C. Blakemore, Steven V. LeyAbstract:The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions have dominated in the development of C-C bond forming processes. A desire to reduce the reliance on precious metals and a need to obtain products with very low levels of metal impurities has brought a renewed focus on metal-free coupling processes. Here, we report the in situ preparation of reactive allylic and benzylic Boronic Acids, obtained by reacting flow-generated diazo compounds with Boronic Acids, and their application in controlled iterative C-C bond forming reactions is described. Thus far we have shown the formation of up to three C-C bonds in a sequence including the final trapping of a reactive Boronic acid species with an aldehyde to generate a range of new chemical structures.
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metal free coupling of saturated heterocyclic sulfonylhydrazones with Boronic Acids
ChemInform, 2014Co-Authors: Daniel M. Allwood, David C. Blakemore, Alan Daniel Brown, Steven V. LeyAbstract:A procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic sulfonylhydrazones with aryl Boronic Acids is developed.
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metal free coupling of saturated heterocyclic sulfonylhydrazones with Boronic Acids
Journal of Organic Chemistry, 2014Co-Authors: Daniel M. Allwood, David C. Blakemore, Alan Daniel Brown, Steven V. LeyAbstract:The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic Boronic Acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2–sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.
Aurelio G Csaky - One of the best experts on this subject based on the ideXlab platform.
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C–C Bond Formation with Boronic Acids and Derivatives by Transition-Metal-Free Conjugate Addition Reactions
Synthesis, 2016Co-Authors: Francisco Sanchez‐sancho, Aurelio G CsakyAbstract:Initially popularized by the Suzuki–Miyaura reaction, Boronic Acids, boronate esters, and trifluoroborates constitute nowadays essential reagents in C–C bond-forming processes. The classic transformations mediated by these reagents require the use of transition metals as catalysts. However, in recent times new reactions in which aryl, alkenyl, and alkynyl derivatives behave as nucleophiles in the absence of transition-metal catalysis have begun to emerge. The purpose of this review is to highlight the most relevant recent advances in C–C bond making reactions by conjugate addition of these types of Boronic Acids under transition-metal-free conditions. 1 Introduction 2 Nucleophilicity of Boronic Acid Derivatives 3 Direct Conjugate Addition Reactions 4 Activation with BF3, Cyanuric Fluoride, or TFAA 5 Activation with BINOL Derivatives 6 Activation with Tartaric Acid and Tartaric Acid Derivatives 7 Conclusions
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trifluoroacetic anhydride promoted tandem conjugate addition of Boronic Acids acetal ring opening
ChemInform, 2012Co-Authors: Silvia Roscales, Aurelio G CsakyAbstract:The conjugate addition of arylethenyl Boronic Acids to acetal-containing α,β-unsaturated carbonyl compounds leads to polysubstituted tetrahydropyran products with formation of 2 C—C bonds and up to 3 stereocenters and formation of a quaternary one.
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trifluoroacetic anhydride promoted tandem conjugate addition of Boronic Acids acetal ring opening
Organic Letters, 2012Co-Authors: Silvia Roscales, Aurelio G CsakyAbstract:A new stereoselective tandem reaction consisting of the metal-free conjugate addition of Boronic Acids followed by an intramolecular ring opening of a cyclic acetal has been disclosed. Optically pure polysubstituted tetrahydropyrans have been synthesized diastereoselectively by this new reaction. Two new C–C bonds and up to three stereocenters are formed in a single step, allowing the generation of quaternary stereocenters.
Fushe Han - One of the best experts on this subject based on the ideXlab platform.
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an efficient suzuki miyaura coupling of aryl sulfamates and Boronic Acids catalyzed by nicl2 dppp
European Journal of Organic Chemistry, 2012Co-Authors: Guojun Chen, Fushe HanAbstract:The SuzukiMiyaura cross-coupling of aryl sulfamates and Boronic Acids was investigated by using [1,3-bis(diphenylphosphanyl)propane]nickel(II) chloride {NiCl2(dppp)} as the catalyst. The results showed that NiCl2(dppp) is a highly active and general catalyst that allows effective SuzukiMiyaura cross-coupling of aryl sulfamates with a slight excess amount of the Boronic acid (1.2 equiv.) in the presence of a low catalyst loading (generally 1.01.5 mol-%). The method also displays broad generality not only to various aryl sulfamates, but also to an array of Boronic Acids. Furthermore, various functional groups are tolerated. These apparent advantages make NiCl2(dppp) a practical and reliable catalyst system for the SuzukiMiyaura coupling of aryl sulfamates.