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  1. Article: One-Pot anti-Michael Regio- and Stereoselective Hydroamination of Activated N-Allenamides

    Hourtoule, Maxime / Zheng, Yongxiang / Perfetto, Anna / Luise, Davide / Ciofini, Ilaria / Miesch, Laurence

    Journal of organic chemistry. 2022 Mar. 28, v. 87, no. 8

    2022  

    Abstract: N-Allenamides, substituted by an ester at the γ-position, were obtained through addition of terminal ynamides with ethyl diazoacetate under copper catalysis for the first time. Regio- and stereoselective hydroamination of those activated N-allenamides ... ...

    Abstract N-Allenamides, substituted by an ester at the γ-position, were obtained through addition of terminal ynamides with ethyl diazoacetate under copper catalysis for the first time. Regio- and stereoselective hydroamination of those activated N-allenamides provided exclusively E-configured captodative enamimes through a one-pot anti-Michael addition. Numerous ynamides as well as various secondary amines were adapted in this process.
    Keywords catalytic activity ; organic chemistry ; stereoselectivity
    Language English
    Dates of publication 2022-0328
    Size p. 5404-5411.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c00302
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

    Z 4' 49/42: Show issues
    Z 7.1: Show issues

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  2. Article ; Online: Direct Synthesis of CF

    Zheng, Yongxiang / Perfetto, Anna / Luise, Davide / Ciofini, Ilaria / Miesch, Laurence

    Organic letters

    2021  Volume 23, Issue 14, Page(s) 5528–5532

    Abstract: The significance of molecules containing difluoromethyl groups is driven by their potential applications in pharmaceutical and agrochemical science. Methods for the incorporation of lightly fluorinated groups such as ... ...

    Abstract The significance of molecules containing difluoromethyl groups is driven by their potential applications in pharmaceutical and agrochemical science. Methods for the incorporation of lightly fluorinated groups such as CF
    Language English
    Publishing date 2021-06-30
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.1c01876
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: One-Pot anti-Michael Regio- and Stereoselective Hydroamination of Activated

    Hourtoule, Maxime / Zheng, Yongxiang / Perfetto, Anna / Luise, Davide / Ciofini, Ilaria / Miesch, Laurence

    The Journal of organic chemistry

    2022  Volume 87, Issue 8, Page(s) 5404–5411

    Abstract: ... ...

    Abstract N
    MeSH term(s) Amines ; Catalysis ; Copper ; Stereoisomerism
    Chemical Substances Amines ; Copper (789U1901C5)
    Language English
    Publishing date 2022-03-28
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c00302
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
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    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  4. Article ; Online: Copper-Catalyzed Synthesis of Terminal vs. Fluorine-Substituted N-Allenamides via Addition of Diazo Compounds to Terminal Ynamides.

    Zheng, Yongxiang / Moegle, Baptiste / Ghosh, Santanu / Perfetto, Anna / Luise, Davide / Ciofini, Ilaria / Miesch, Laurence

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 28, Issue 1, Page(s) e202103598

    Abstract: A copper-mediated coupling reaction between ynamides and diazo-compounds to produce N-allenamides is reported for the first time. This method enables facile and rapid access to terminal N-allenamides by using commercially available TMS-diazomethane with ... ...

    Abstract A copper-mediated coupling reaction between ynamides and diazo-compounds to produce N-allenamides is reported for the first time. This method enables facile and rapid access to terminal N-allenamides by using commercially available TMS-diazomethane with wide functional group compatibility on the nitrogen. Furthermore, the ubiquity of molecules containing a fluorine moiety in medicine, in agricultural, and material science requires the continuous search of new building blocks, including this unique surrogate. The CuI/diazo protocol was successfully applied to the synthesis of fluorine-substituted N-allenamides. DFT calculations provided insights in the mechanism involved.
    MeSH term(s) Azo Compounds ; Catalysis ; Copper ; Fluorine
    Chemical Substances Azo Compounds ; Fluorine (284SYP0193) ; Copper (789U1901C5)
    Language English
    Publishing date 2021-12-09
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202103598
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group*.

    Force, Guillaume / Perfetto, Anna / Mayer, Robert J / Ciofini, Ilaria / Lebœuf, David

    Angewandte Chemie (International ed. in English)

    2021  Volume 60, Issue 36, Page(s) 19843–19851

    Abstract: Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progress made towards their synthesis, notably from seco-acids, a ... ...

    Abstract Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progress made towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables a convenient access to macrolactones, macrodiolides and esters with a broad versatility. Kinetic studies and DFT computations were performed to rationalize the reactivity of the pentafluorophenyl group in macrolactonization reactions.
    Language English
    Publishing date 2021-08-03
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202105882
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: General Density-Based Index to Analyze Charge Transfer Phenomena: From Models to Butterfly Molecules.

    Huet, Léon / Perfetto, Anna / Muniz-Miranda, Francesco / Campetella, Marco / Adamo, Carlo / Ciofini, Ilaria

    Journal of chemical theory and computation

    2020  Volume 16, Issue 7, Page(s) 4543–4553

    Abstract: We present a new formula and implementation for a descriptor enabling quantification of the electron-hole distance associated with a charge transfer of an optical transition, on the basis of the knowledge of the densities of the electronic ground and ... ...

    Abstract We present a new formula and implementation for a descriptor enabling quantification of the electron-hole distance associated with a charge transfer of an optical transition, on the basis of the knowledge of the densities of the electronic ground and excited states. This index is able to define a charge-transfer length even for systems that would be otherwise difficult to treat, like symmetric molecules, while maintaining a very low computational cost and the possibility to be coupled to any method providing ground and excited state electron densities. After a benchmark of its performance on a series of push-pull molecules, the index has been applied to a set of large symmetric luminophores, the so-called "butterfly molecules", showing promising applications in optoelectronics, to highlight its potential use in the design of new compounds.
    Language English
    Publishing date 2020-06-18
    Publishing country United States
    Document type Journal Article
    ISSN 1549-9626
    ISSN (online) 1549-9626
    DOI 10.1021/acs.jctc.0c00296
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies.

    Lecroq, William / Schleinitz, Jules / Billoue, Mallaury / Perfetto, Anna / Gaumont, Annie-Claude / Lalevée, Jacques / Ciofini, Ilaria / Grimaud, Laurence / Lakhdar, Sami

    Chemphyschem : a European journal of chemical physics and physical chemistry

    2021  Volume 22, Issue 12, Page(s) 1237–1242

    Abstract: We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using ... ...

    Abstract We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.
    Language English
    Publishing date 2021-05-28
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2025223-7
    ISSN 1439-7641 ; 1439-4235
    ISSN (online) 1439-7641
    ISSN 1439-4235
    DOI 10.1002/cphc.202100108
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article ; Online: Silver(I) Oxide-/DBU-Promoted Synthesis of Dihydrofuran Units through Allenyl Silver Formation.

    Yu, Bao / Perfetto, Anna / Allievi, Luca / Dhambri, Sabrina / Rager, Marie-Noelle / Selkti, Mohamed / Ciofini, Ilaria / Lannou, Marie-Isabelle / Sorin, Geoffroy

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2020  Volume 26, Issue 72, Page(s) 17455–17461

    Abstract: A formal [3+2] cyclization mediated by silver(I) oxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is described herein. Through a broad variety of carbonyl compounds, this system can promote cyclization reactions with high yield (up to 85 %) and ... ...

    Abstract A formal [3+2] cyclization mediated by silver(I) oxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is described herein. Through a broad variety of carbonyl compounds, this system can promote cyclization reactions with high yield (up to 85 %) and diastereoselectivity (up to 95:5) for a straightforward access to complex and congested dihydrofuran derivatives in one step under mild conditions. Based on DFT studies, the proposed mechanism would involve an allenyl silver intermediate.
    Language English
    Publishing date 2020-12-01
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202002696
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: Mechanochromic LLDPE Films Doped with NIR Reflective Paliogen Black.

    Micheletti, Cosimo / Minei, Pierpaolo / Carlotti, Marco / Mattoli, Virgilio / Muniz-Miranda, Francesco / Perfetto, Anna / Ciofini, Ilaria / Adamo, Carlo / Ruggeri, Giacomo / Pucci, Andrea

    Macromolecular rapid communications

    2020  Volume 42, Issue 1, Page(s) e2000426

    Abstract: The perylene bisimide derivative Paliogen Black (P-black) is proposed as a new chromogenic probe that shows visible (vis) and near-infrared (NIR) responses after mechanical solicitations of host linear low-density polyethylene (LLDPE) films. P-black is ... ...

    Abstract The perylene bisimide derivative Paliogen Black (P-black) is proposed as a new chromogenic probe that shows visible (vis) and near-infrared (NIR) responses after mechanical solicitations of host linear low-density polyethylene (LLDPE) films. P-black is reported to display strong absorption in the vis spectrum and unusual reflective and cooling features in the NIR region. Uniaxial deformation of the 2.5, 5, and 10 wt% P-black/LLDPE films yields a dichroic absorption under polarized light with color variations attributed by the computational analysis to the distinct anisotropic behavior of the transition dipole moments of P-black chromophores. When LLDPE films are deformed, P-black aggregates reduce their size from ≈30-40 µm to ≈5-10 µm that, in turn, causes reflectivity losses of about 30-40% at the maximum elongation. This gives rise to warming of 5-6 °C of the locally oriented film placed in contact with a black substrate under the illumination with an IR lamp for 5 s. These features combined with the high sensitivity of the vis-NIR response toward mechanical solicitations render P-black as a new solution to detect uniaxial deformations of plastic films through both optical and thermal outputs.
    MeSH term(s) Plastics ; Polyethylene
    Chemical Substances Plastics ; Polyethylene (9002-88-4)
    Language English
    Publishing date 2020-10-21
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1475027-2
    ISSN 1521-3927 ; 1022-1336
    ISSN (online) 1521-3927
    ISSN 1022-1336
    DOI 10.1002/marc.202000426
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