Ortho-Deuteration of Aromatic Aldehydes via a Transient Directing Group-Enabled Pd-Catalyzed Hydrogen Isotope Exchange

2021 ◽  
Vol 86 (19) ◽  
pp. 13350-13359
Author(s):  
Junhua Kong ◽  
Zhi-Jiang Jiang ◽  
Jiayuan Xu ◽  
Yan Li ◽  
Hong Cao ◽  
...  
Keyword(s):  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Aromatic Aldehydes ◽  
Hydrogen Isotope Exchange ◽  
Directing Group

scholarly journals A quantitative empirical directing group scale for selectivity in iridium-catalysed hydrogen isotope exchange reactions

2020 ◽  
Vol 10 (21) ◽  
pp. 7249-7255
Author(s):  
Daria S. Timofeeva ◽  
David M. Lindsay ◽  
William J. Kerr ◽  
David J. Nelson
Keyword(s):  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Exchange Reactions ◽  
Hydrogen Isotope Exchange ◽  
Directing Group

Competition hydrogen isotope exchange (HIE) experiments are used to construct quantitative directing group scales for two catalysts; these can be used to predict the outcomes of HIE reactions of substrates with multiple directing groups.

scholarly journals Quantitative Prediction of Selectivity in Iridium-Catalysed Hydrogen Isotope Exchange Reactions

2020 ◽  
Author(s):  
Daria Timofeeva ◽  
David Lindsay ◽  
William Kerr ◽  
David Nelson
Keyword(s):  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Quantitative Prediction ◽  
Iridium Complexes ◽  
Exchange Reactions ◽  
Hydrogen Isotope Exchange ◽  
Wide Range ◽  
Directing Group ◽  
And Control

A pallette of commonly used directing groups, including various pharmaceutically relevant nitrogen-containing heterocycles, are quantitatively ranked based on the results of intermolecular hydrogen isotope exchange competition reactions using two iridium complexes: [Ir(COD)(IMes)(PPh3)][BArF24] and [IrCl(COD)(IMes)]. The directing group power scales that have been constructred from these data reveal a wide range of reactivity covering four orders of magnitude. Intramolecular competition experiments have demonstrated that the obtained reactivity scale provides accurate predictions of regioselectivity within molecules with multiple competing directing groups. This work contributes to our understanding and control of regioselectivity in metal-catalysed C-H activation reactions.

scholarly journals Quantitative Prediction of Selectivity in Iridium-Catalysed Hydrogen Isotope Exchange Reactions

2020 ◽  
Author(s):  
Daria Timofeeva ◽  
David Lindsay ◽  
William Kerr ◽  
David Nelson
Keyword(s):  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Quantitative Prediction ◽  
Iridium Complexes ◽  
Exchange Reactions ◽  
Hydrogen Isotope Exchange ◽  
Wide Range ◽  
Directing Group ◽  
And Control

A pallette of commonly used directing groups, including various pharmaceutically relevant nitrogen-containing heterocycles, are quantitatively ranked based on the results of intermolecular hydrogen isotope exchange competition reactions using two iridium complexes: [Ir(COD)(IMes)(PPh3)][BArF24] and [IrCl(COD)(IMes)]. The directing group power scales that have been constructred from these data reveal a wide range of reactivity covering four orders of magnitude. Intramolecular competition experiments have demonstrated that the obtained reactivity scale provides accurate predictions of regioselectivity within molecules with multiple competing directing groups. This work contributes to our understanding and control of regioselectivity in metal-catalysed C-H activation reactions.

scholarly journals Are rate and selectivity correlated in iridium-catalysed hydrogen isotope exchange reactions?

2021 ◽  
Author(s):  
Daria S. Timofeeva ◽  
David M Lindsay ◽  
W. J. Kerr ◽  
David James Nelson
Keyword(s):  
Functional Groups ◽  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Reaction Rate ◽  
Exchange Reactions ◽  
Reaction Selectivity ◽  
Hydrogen Isotope Exchange ◽  
The Relationship

Herein we examine the relationship between reaction rate and reaction selectivity in iridium-catalysed hydrogen isotope exchange (HIE) reactions directed by Lewis basic functional groups. We have recently develped a directing...

Hydrogen isotope exchange between D2 and H2O catalyzed by platinum plate

1989 ◽  
Vol 67 (5) ◽  
pp. 857-861 ◽  
Author(s):  
Shin-Ichi Miyamoto ◽  
Tetsuo Sakka ◽  
Matae Iwasaki
Keyword(s):  
Kinetic Model ◽  
Exchange Reaction ◽  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Reaction Rate ◽  
Hydrogen Adsorption ◽  
Platinum Catalyst ◽  
Isotope Exchange Reaction ◽  
Hydrogen Isotope Exchange ◽  
Supported Platinum

The reaction rate of hydrogen isotope exchange between D2 and H2O catalyzed by platinum plate is studied. The exchange reaction is described with the kinetic model which is the modification of that for the exchange reaction catalyzed by alumina-supported platinum catalyst. For the comparison of experimental results with this model relative amount of the number of sites for hydrogen adsorption was estimated from the initial rate of hydrogen isotope exchange between H2 and D2 on the same surface. The results show that the kinetic model is applicable for the plate catalyst if the number of the sites for hydrogen absorption, which is very sensitive to the surface state of the catalyst, was estimated not from the macroscopic surface area but from our scheme. Keywords: hydrogen isotope exchange reaction, platinum plate as catalyst.

Two-film effects on the kinetics of hydrogen isotope exchange between CHCl3 and D2O in two liquid phase system

1993 ◽  
Vol 25 (5) ◽  
pp. 363-374
Author(s):  
Matae Iwasaki ◽  
Tetsuo Sakka ◽  
Shigeyuki Ohashi ◽  
Yoshikazu Miyake ◽  
Hiroshi Matsushita
Keyword(s):  
Liquid Phase ◽  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Phase System ◽  
Hydrogen Isotope Exchange ◽  
Kinetics Of
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