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Fabien Gagosz - One of the best experts on this subject based on the ideXlab platform.
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Use of a Benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates.
Chemical Communications, 2018Co-Authors: Hirohito Hayashi, Fabien Gagosz, Atsushi Kaga, Bin Wang, Shunsuke ChibaAbstract:A new protocol for the anti-Markovnikov hydrofunctionalization of alkenyl alcohol O-Bn ethers was developed using xanthates as functionalizing agents in the presence of lauroyl peroxide as a radical initiator and a stoichiometric oxidant. The Benzyl Group serves as a traceless hydrogen donor in the remote radical hydrogen atom transfer event during the process.
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anti markovnikov hydrofunctionalization of alkenes use of a Benzyl Group as a traceless redox active hydrogen donor
Angewandte Chemie, 2017Co-Authors: Geoffroy Hervé Lonca, Fabien Gagosz, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra TejoAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes, that utilizes a Benzyl Group as a traceless redox-active hydrogen donor, has been developed. Under copper catalysis and in the presence of CF3- or N3-containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives could be regioselectivity hydrofunctionalized. A similar principle was also applied to the hydrofunctionalization of alkenols.
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Anti-Markovnikov Hydrofunctionalization of Alkenes
Angewandte Chemie International Edition, 2017Co-Authors: Geoffroy Hervé Lonca, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra Tejo, Fabien GagoszAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a Benzyl Group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3 - or N3 -containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols.
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Anti‐Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox‐Active Hydrogen Donor
Angewandte Chemie International Edition, 2017Co-Authors: Geoffroy Hervé Lonca, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra Tejo, Fabien GagoszAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes, that utilizes a Benzyl Group as a traceless redox-active hydrogen donor, has been developed. Under copper catalysis and in the presence of CF3- or N3-containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives could be regioselectivity hydrofunctionalized. A similar principle was also applied to the hydrofunctionalization of alkenols.
Kuangsen Sung - One of the best experts on this subject based on the ideXlab platform.
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s1 s0 potential energy surfaces experience different types of restricted rotation restricted z e photoisomerization and e z thermoisomerization by an out of plane Benzyl Group or in plane m pyridinium Group
Journal of Physical Chemistry A, 2019Co-Authors: Robert Sung, Kuangsen SungAbstract:Any method that can enhance the fluorescence of fluorophores is highly desirable. Fluorescence enhancement accomplished by restricted Z/ E photoisomerization through intramolecular steric hindrance or relatively high bond order of a C═C double bond in a S1 excited state has rarely been studied. In this article, we used green fluorescent protein (GFP) chromophore analogues as a model to get new physical insights into the restricted Z/ E photoisomerization and E/ Z thermoisomerization phenomena. We found that the S1 and S0 potential energy surfaces (PESs) of the GFP chromophore analogues experience two dramatically different types of restricted rotation, and 2b can be a representative example. In its S1 PES, it is not the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group but the relatively high bond order of the I-bond in the S1 excited state of 2b that makes it have a higher barrier for the Z/ E photoisomerization, a smaller Z/ E photoisomerization quantum yield, and a higher fluorescence quantum yield. In its S0 PES, it is not the reduced bond order of the I-bond in the S0 ground state of 2b but the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group that makes it have an extra higher barrier for E/ Z thermoisomerization and a much smaller E/ Z thermoisomerization rate constant.
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S1/S0 Potential Energy Surfaces Experience Different Types of Restricted Rotation: Restricted Z/ E Photoisomerization and E/ Z Thermoisomerization by an Out-of-Plane Benzyl Group or In-Plane m-Pyridinium Group?
The Journal of Physical Chemistry A, 2019Co-Authors: Robert Sung, Kuangsen SungAbstract:Any method that can enhance the fluorescence of fluorophores is highly desirable. Fluorescence enhancement accomplished by restricted Z/ E photoisomerization through intramolecular steric hindrance or relatively high bond order of a C═C double bond in a S1 excited state has rarely been studied. In this article, we used green fluorescent protein (GFP) chromophore analogues as a model to get new physical insights into the restricted Z/ E photoisomerization and E/ Z thermoisomerization phenomena. We found that the S1 and S0 potential energy surfaces (PESs) of the GFP chromophore analogues experience two dramatically different types of restricted rotation, and 2b can be a representative example. In its S1 PES, it is not the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group but the relatively high bond order of the I-bond in the S1 excited state of 2b that makes it have a higher barrier for the Z/ E photoisomerization, a smaller Z/ E photoisomerization quantum yield, and a higher fluorescence quantum yield. In its S0 PES, it is not the reduced bond order of the I-bond in the S0 ground state of 2b but the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group that makes it have an extra higher barrier for E/ Z thermoisomerization and a much smaller E/ Z thermoisomerization rate constant.
B. M. Bhawal - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of N1-unsubstituted β-lactams via a facile deprotection of N1-[(α-thiophenyl)Benzyl] Group
Tetrahedron, 1998Co-Authors: K. Karupaiyan, V. Srirajan, A. R. A. S. Deshmukh, B. M. BhawalAbstract:Abstract A diastereoselective synthesis of (±) cis-β-lactams (5 & 6) via cycloaddition reactions of N1-(α-thiophenyl)Benzyl imines (3) with acid chlorides (4) in the presence of triethylamine is described. The deprotection of N1-(α-thiophenyl)Benzyl Group has been achieved by oxidation using potassium persulfate to give N-unsubstituted β-lactams (7) in good yields.
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synthesis of n1 unsubstituted β lactams introducing n1 1 thiophenyl Benzyl as an n protecting Group
Tetrahedron Letters, 1997Co-Authors: K. Karupaiyan, V. Srirajan, A. R. A. S. Deshmukh, B. M. BhawalAbstract:Abstract A diastereoselective synthesis of (±) cis - β -lactams ( 5 & 6 ) via cycloaddition reaction of N 1 -(α-thiophenyl)Benzyl imines ( 3 ) with acid chlorides ( 4 ) in the presence of triethyl amine is described. Deprotection of N 1 -(α-thiophenyl)-Benzyl Group was achieved in good yields by oxidation using potassium persulfate.
Robert Sung - One of the best experts on this subject based on the ideXlab platform.
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s1 s0 potential energy surfaces experience different types of restricted rotation restricted z e photoisomerization and e z thermoisomerization by an out of plane Benzyl Group or in plane m pyridinium Group
Journal of Physical Chemistry A, 2019Co-Authors: Robert Sung, Kuangsen SungAbstract:Any method that can enhance the fluorescence of fluorophores is highly desirable. Fluorescence enhancement accomplished by restricted Z/ E photoisomerization through intramolecular steric hindrance or relatively high bond order of a C═C double bond in a S1 excited state has rarely been studied. In this article, we used green fluorescent protein (GFP) chromophore analogues as a model to get new physical insights into the restricted Z/ E photoisomerization and E/ Z thermoisomerization phenomena. We found that the S1 and S0 potential energy surfaces (PESs) of the GFP chromophore analogues experience two dramatically different types of restricted rotation, and 2b can be a representative example. In its S1 PES, it is not the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group but the relatively high bond order of the I-bond in the S1 excited state of 2b that makes it have a higher barrier for the Z/ E photoisomerization, a smaller Z/ E photoisomerization quantum yield, and a higher fluorescence quantum yield. In its S0 PES, it is not the reduced bond order of the I-bond in the S0 ground state of 2b but the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group that makes it have an extra higher barrier for E/ Z thermoisomerization and a much smaller E/ Z thermoisomerization rate constant.
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S1/S0 Potential Energy Surfaces Experience Different Types of Restricted Rotation: Restricted Z/ E Photoisomerization and E/ Z Thermoisomerization by an Out-of-Plane Benzyl Group or In-Plane m-Pyridinium Group?
The Journal of Physical Chemistry A, 2019Co-Authors: Robert Sung, Kuangsen SungAbstract:Any method that can enhance the fluorescence of fluorophores is highly desirable. Fluorescence enhancement accomplished by restricted Z/ E photoisomerization through intramolecular steric hindrance or relatively high bond order of a C═C double bond in a S1 excited state has rarely been studied. In this article, we used green fluorescent protein (GFP) chromophore analogues as a model to get new physical insights into the restricted Z/ E photoisomerization and E/ Z thermoisomerization phenomena. We found that the S1 and S0 potential energy surfaces (PESs) of the GFP chromophore analogues experience two dramatically different types of restricted rotation, and 2b can be a representative example. In its S1 PES, it is not the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group but the relatively high bond order of the I-bond in the S1 excited state of 2b that makes it have a higher barrier for the Z/ E photoisomerization, a smaller Z/ E photoisomerization quantum yield, and a higher fluorescence quantum yield. In its S0 PES, it is not the reduced bond order of the I-bond in the S0 ground state of 2b but the intramolecular steric hindrance between the out-of-plane Benzyl Group and the in-plane m-pyridinium Group that makes it have an extra higher barrier for E/ Z thermoisomerization and a much smaller E/ Z thermoisomerization rate constant.
Geoffroy Hervé Lonca - One of the best experts on this subject based on the ideXlab platform.
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Anti-Markovnikov Hydrofunctionalization of Alkenes
Angewandte Chemie International Edition, 2017Co-Authors: Geoffroy Hervé Lonca, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra Tejo, Fabien GagoszAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a Benzyl Group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3 - or N3 -containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols.
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anti markovnikov hydrofunctionalization of alkenes use of a Benzyl Group as a traceless redox active hydrogen donor
Angewandte Chemie, 2017Co-Authors: Geoffroy Hervé Lonca, Fabien Gagosz, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra TejoAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes, that utilizes a Benzyl Group as a traceless redox-active hydrogen donor, has been developed. Under copper catalysis and in the presence of CF3- or N3-containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives could be regioselectivity hydrofunctionalized. A similar principle was also applied to the hydrofunctionalization of alkenols.
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Anti‐Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox‐Active Hydrogen Donor
Angewandte Chemie International Edition, 2017Co-Authors: Geoffroy Hervé Lonca, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra Tejo, Fabien GagoszAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes, that utilizes a Benzyl Group as a traceless redox-active hydrogen donor, has been developed. Under copper catalysis and in the presence of CF3- or N3-containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives could be regioselectivity hydrofunctionalized. A similar principle was also applied to the hydrofunctionalization of alkenols.