The Experts below are selected from a list of 114 Experts worldwide ranked by ideXlab platform
Sanggi Lee - One of the best experts on this subject based on the ideXlab platform.
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Pd-Catalyzed Aminocarbonylation of the Blaise Reaction Intermediate: One-Pot Synthesis of (Z)‑3-Methyleneisoindolin-1-ones from Nitriles
2016Co-Authors: Zi Xuan, Da Jung Jung, Hyun Ji Jeon, Sanggi LeeAbstract:A highly efficient method for the one-pot synthesis of stereocontrolled (Z)-3-methyleneisoindolin-1-ones was developed starting from 2-bromoarylnitriles via tandem sequential Reaction with a Reformatsky reagent (Blaise Reaction), followed by Pd-catalyzed intramolecular aminocarbonylation with carbon monoxide at 1 atm pressure. It has been found that the conformational flexibility of the bisphophine ligand is of great importance to the success of this tandem aminocarbonylation Reaction
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tandem synthesis of polysubstituted pyridines via the indium iii triflate catalyzed cycloaddition oxidative aromatization of Blaise Reaction intermediates with α β unsaturated ketones
ChemInform, 2015Co-Authors: Zi Xuan, Kris Rathwell, Sanggi LeeAbstract:In absence of oxygen in the second step, a subsequent oxidation stage is needed to achieve full aromatization of the pyridine ring.
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Tandem Blaise/Palladium-Catalyzed Ullmann Coupling for the One-Pot Synthesis of Enamino Ester-Functionalized Biaryls from Nitriles
2015Co-Authors: Zi Xuan, Ju Hyun Kim, Sanggi LeeAbstract:A novel Pd-catalyzed Ullmann-type homocoupling Reaction of the Blaise Reaction intermediate generated by the Reaction of 2-bromo arylnitriles and a Reformatsky reagent has been developed for one-pot synthesis of enamino ester-functionalized biaryls 2 in good yields. The 2,2′-substituted enamine moieties of the coupling products could be cyclized under acidic conditions through the conjugate addition/deamination cascade to afford the seven-membered N-heterocyclics 3 with biaryl backbone in excellent yields
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tandem synthesis of polysubstituted pyridines via the indium iii triflate catalyzed cycloaddition oxidative aromatization of Blaise Reaction intermediates with α β unsaturated ketones
Asian Journal of Organic Chemistry, 2014Co-Authors: Zi Xuan, Kris Rathwell, Sanggi LeeAbstract:A tandem one-pot method for the construction of polysubstituted pyridines with complete control of the substitution pattern has been developed. The zinc bromide β-enamino ester intermediates of the Blaise Reaction of simple nitriles with a Reformatsky reagent undergo Michael addition with conjugated ketones in the presence of a catalytic amount of In(OTf)3. Final intramolecular cyclization and oxidative aromatization yields polysubstituted pyridines in this tandem one-pot cascade.
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tandem Blaise retro Blaise Reaction for the nitrile mediated regioselective intermolecular addition of unstabilized zinc ester enolates reformatsky reagents to 1 alkynes and 1 3 enynes
ChemInform, 2014Co-Authors: Ju Hyun Kim, Yu Sung Chun, Sanggi LeeAbstract:A broad range of alkynes can be applied to the title Reaction and yield the corresponding acrylates in good yields and regioselectivities.
Yu Sung Chun - One of the best experts on this subject based on the ideXlab platform.
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tandem Blaise retro Blaise Reaction for the nitrile mediated regioselective intermolecular addition of unstabilized zinc ester enolates reformatsky reagents to 1 alkynes and 1 3 enynes
ChemInform, 2014Co-Authors: Ju Hyun Kim, Yu Sung Chun, Sanggi LeeAbstract:A broad range of alkynes can be applied to the title Reaction and yield the corresponding acrylates in good yields and regioselectivities.
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tandem Blaise retro Blaise Reaction for the nitrile mediated regioselective intermolecular addition of unstabilized zinc ester enolates reformatsky reagents to 1 alkynes and 1 3 enynes
Journal of Organic Chemistry, 2013Co-Authors: Ju Hyun Kim, Yu Sung Chun, Sanggi LeeAbstract:We report the novel use of a nitrile as a mediator to achieve the regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1-alkynes and 1,3-enynes. This Reaction is made possible by a reversible addition of enolates to a nitrile (Blaise Reaction), generating a zinc aza-enolate that, unlike zinc ester enolates, can add intermolecularly to 1-alkynes and 1,3-enynes. Subsequent removal of the nitrile through a retro-Blaise Reaction generates the targeted addition product. This method is combined with a Diels–Alder Reaction and subsequent oxidative aromatization, providing a tandem one-pot de novo construction of α-arylated alkanoates from Reformatsky reagents.
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an expedient and divergent tandem one pot synthesis of pyrimidin 2 4 diones using the Blaise Reaction intermediate
Organic Letters, 2013Co-Authors: Yu Sung Chun, Zi XuanAbstract:A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives is developed. In the presence of 10 mol % of Cu(OAc)2, the α-substituted Blaise Reaction intermediates (R2 ≠ H) reacted with isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the α-unsubstituted Blaise Reaction intermediate (R2 = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem Reactions.
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tandem one pot synthesis of polysubstituted pyridines using the Blaise Reaction intermediate and 1 3 enynes
ChemInform, 2012Co-Authors: Yu Sung Chun, Young Ok KoAbstract:Sequential Reaction of nitriles, Reformatsky reagents and 1,3-enynes proceeds with complete regio- and chemoselectivity to provide the polysubstituted pyridines.
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Cu(OAc)2‑Catalyzed Tandem Blaise/Pinner-Type Reaction for One-Pot Synthesis of Pyrimidin-4-ones
2012Co-Authors: Yu Sung Chun, Ju Hyun Kim, Suh Young Choi, Sanggi LeeAbstract:A novel tandem Blaise/Pinner-type Reaction for the one-pot synthesis of pyrimidin-4-ones is described. The Blaise Reaction intermediate, formed by addition of a Reformatsky reagent to a nitrile, reacted with a second nitrile chemoselectively in the presence of a catalytic amount of Cu(OAc)2 to afford pyrimidin-4-ones
Hyunik Shin - One of the best experts on this subject based on the ideXlab platform.
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chemoselective intramolecular alkylation of the Blaise Reaction intermediates tandem one pot synthesis of exo cyclic enaminoesters and their applications toward the synthesis of n heterocyclic compounds
ChemInform, 2012Co-Authors: Ju Hyun Kim, Hyunik Shin, Sanggi LeeAbstract:Coupling of nitriles (I) and (VII) with Reformatsky reagents, generated from bromides (II) and (V), followed by treatment with NaN(Tms)2 allows an efficient access to exo-cyclic enaminoesters.
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chemoselective intramolecular alkylation of the Blaise Reaction intermediates tandem one pot synthesis of exo cyclic enaminoesters and their applications toward the synthesis of n heterocyclic compounds
Journal of Organic Chemistry, 2012Co-Authors: Ju Hyun Kim, Hyunik Shin, Sanggi LeeAbstract:The intramolecular alkylative reactivity and N/C selectivity of the various Blaise Reaction intermediates, which are formed from the Reaction of the Reformatsky reagents with ω-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.
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Chemoselective Intramolecular Alkylation of the Blaise Reaction Intermediates: Tandem One-Pot Synthesis of exo-Cyclic Enaminoesters and Their Applications toward the Synthesis of N-Heterocyclic Compounds
2012Co-Authors: Ju Hyun Kim, Hyunik Shin, Sanggi LeeAbstract:The intramolecular alkylative reactivity and N/C selectivity of the various Blaise Reaction intermediates, which are formed from the Reaction of the Reformatsky reagents with ω-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles
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tandem Blaise nenitzescu Reaction one pot synthesis of 5 hydroxy α aminomethylene benzofuran 2 3h ones from nitriles
ChemInform, 2011Co-Authors: Yu Sung Chun, Hyunik Shin, Ka Yeon Ryu, Ju Hyun Kim, Sanggi LeeAbstract:Direct Reaction of the zinc bromide complex of β-enamino esters (Blaise Reaction intermediate) with benzoquinones affords title aminomethylenebenzofuranones, e.g. (IV), (VI), (VIII) or (X), instead of the expected indoles (Nenitzescu products).
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tandem one pot synthesis of α aminomethylene γ butyrolactones via regioselective epoxide ring opening with the Blaise Reaction intermediate
ChemInform, 2011Co-Authors: Young Ok Ko, Yu Sung Chun, Hyunik ShinAbstract:The Reaction of the Reformatsky reagent derived from ethyl bromoacetate and subsequent coupling of the resulting Blaise intermediate with oxiranes allows the synthesis of the title compounds in fair yields.
Ju Hyun Kim - One of the best experts on this subject based on the ideXlab platform.
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Tandem Blaise/Palladium-Catalyzed Ullmann Coupling for the One-Pot Synthesis of Enamino Ester-Functionalized Biaryls from Nitriles
2015Co-Authors: Zi Xuan, Ju Hyun Kim, Sanggi LeeAbstract:A novel Pd-catalyzed Ullmann-type homocoupling Reaction of the Blaise Reaction intermediate generated by the Reaction of 2-bromo arylnitriles and a Reformatsky reagent has been developed for one-pot synthesis of enamino ester-functionalized biaryls 2 in good yields. The 2,2′-substituted enamine moieties of the coupling products could be cyclized under acidic conditions through the conjugate addition/deamination cascade to afford the seven-membered N-heterocyclics 3 with biaryl backbone in excellent yields
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tandem Blaise retro Blaise Reaction for the nitrile mediated regioselective intermolecular addition of unstabilized zinc ester enolates reformatsky reagents to 1 alkynes and 1 3 enynes
ChemInform, 2014Co-Authors: Ju Hyun Kim, Yu Sung Chun, Sanggi LeeAbstract:A broad range of alkynes can be applied to the title Reaction and yield the corresponding acrylates in good yields and regioselectivities.
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tandem Blaise retro Blaise Reaction for the nitrile mediated regioselective intermolecular addition of unstabilized zinc ester enolates reformatsky reagents to 1 alkynes and 1 3 enynes
Journal of Organic Chemistry, 2013Co-Authors: Ju Hyun Kim, Yu Sung Chun, Sanggi LeeAbstract:We report the novel use of a nitrile as a mediator to achieve the regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1-alkynes and 1,3-enynes. This Reaction is made possible by a reversible addition of enolates to a nitrile (Blaise Reaction), generating a zinc aza-enolate that, unlike zinc ester enolates, can add intermolecularly to 1-alkynes and 1,3-enynes. Subsequent removal of the nitrile through a retro-Blaise Reaction generates the targeted addition product. This method is combined with a Diels–Alder Reaction and subsequent oxidative aromatization, providing a tandem one-pot de novo construction of α-arylated alkanoates from Reformatsky reagents.
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chemoselective intramolecular alkylation of the Blaise Reaction intermediates tandem one pot synthesis of exo cyclic enaminoesters and their applications toward the synthesis of n heterocyclic compounds
ChemInform, 2012Co-Authors: Ju Hyun Kim, Hyunik Shin, Sanggi LeeAbstract:Coupling of nitriles (I) and (VII) with Reformatsky reagents, generated from bromides (II) and (V), followed by treatment with NaN(Tms)2 allows an efficient access to exo-cyclic enaminoesters.
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chemoselective intramolecular alkylation of the Blaise Reaction intermediates tandem one pot synthesis of exo cyclic enaminoesters and their applications toward the synthesis of n heterocyclic compounds
Journal of Organic Chemistry, 2012Co-Authors: Ju Hyun Kim, Hyunik Shin, Sanggi LeeAbstract:The intramolecular alkylative reactivity and N/C selectivity of the various Blaise Reaction intermediates, which are formed from the Reaction of the Reformatsky reagents with ω-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.
Zi Xuan - One of the best experts on this subject based on the ideXlab platform.
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Pd-Catalyzed Aminocarbonylation of the Blaise Reaction Intermediate: One-Pot Synthesis of (Z)‑3-Methyleneisoindolin-1-ones from Nitriles
2016Co-Authors: Zi Xuan, Da Jung Jung, Hyun Ji Jeon, Sanggi LeeAbstract:A highly efficient method for the one-pot synthesis of stereocontrolled (Z)-3-methyleneisoindolin-1-ones was developed starting from 2-bromoarylnitriles via tandem sequential Reaction with a Reformatsky reagent (Blaise Reaction), followed by Pd-catalyzed intramolecular aminocarbonylation with carbon monoxide at 1 atm pressure. It has been found that the conformational flexibility of the bisphophine ligand is of great importance to the success of this tandem aminocarbonylation Reaction
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tandem synthesis of polysubstituted pyridines via the indium iii triflate catalyzed cycloaddition oxidative aromatization of Blaise Reaction intermediates with α β unsaturated ketones
ChemInform, 2015Co-Authors: Zi Xuan, Kris Rathwell, Sanggi LeeAbstract:In absence of oxygen in the second step, a subsequent oxidation stage is needed to achieve full aromatization of the pyridine ring.
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Tandem Blaise/Palladium-Catalyzed Ullmann Coupling for the One-Pot Synthesis of Enamino Ester-Functionalized Biaryls from Nitriles
2015Co-Authors: Zi Xuan, Ju Hyun Kim, Sanggi LeeAbstract:A novel Pd-catalyzed Ullmann-type homocoupling Reaction of the Blaise Reaction intermediate generated by the Reaction of 2-bromo arylnitriles and a Reformatsky reagent has been developed for one-pot synthesis of enamino ester-functionalized biaryls 2 in good yields. The 2,2′-substituted enamine moieties of the coupling products could be cyclized under acidic conditions through the conjugate addition/deamination cascade to afford the seven-membered N-heterocyclics 3 with biaryl backbone in excellent yields
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tandem synthesis of polysubstituted pyridines via the indium iii triflate catalyzed cycloaddition oxidative aromatization of Blaise Reaction intermediates with α β unsaturated ketones
Asian Journal of Organic Chemistry, 2014Co-Authors: Zi Xuan, Kris Rathwell, Sanggi LeeAbstract:A tandem one-pot method for the construction of polysubstituted pyridines with complete control of the substitution pattern has been developed. The zinc bromide β-enamino ester intermediates of the Blaise Reaction of simple nitriles with a Reformatsky reagent undergo Michael addition with conjugated ketones in the presence of a catalytic amount of In(OTf)3. Final intramolecular cyclization and oxidative aromatization yields polysubstituted pyridines in this tandem one-pot cascade.
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an expedient and divergent tandem one pot synthesis of pyrimidin 2 4 diones using the Blaise Reaction intermediate
Organic Letters, 2013Co-Authors: Yu Sung Chun, Zi XuanAbstract:A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives is developed. In the presence of 10 mol % of Cu(OAc)2, the α-substituted Blaise Reaction intermediates (R2 ≠ H) reacted with isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the α-unsubstituted Blaise Reaction intermediate (R2 = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem Reactions.