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Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes
by
Kowalczyk, Rafal
, Dutta, Bishal
, Ghosh, Animesh
, Mahajan, Mayank
, Ge, Haibo
, Maiti, Debabrata
, Mondal, Bhaskar
, Dajek, Maciej
in
119/118
/ 140/131
/ 140/58
/ 639/638/403/933
/ 639/638/549/933
/ 639/638/77/888
/ Alkenes
/ Bonding strength
/ Catalysis
/ Humanities and Social Sciences
/ Hydrocarbons
/ Hydrogen
/ Hydrogen bonding
/ Hydrogen bonds
/ Investigations
/ multidisciplinary
/ Nitrobenzene
/ Palladium
/ Regioselectivity
/ Science
/ Science (multidisciplinary)
/ Substrates
/ Urea
2024
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Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes
by
Kowalczyk, Rafal
, Dutta, Bishal
, Ghosh, Animesh
, Mahajan, Mayank
, Ge, Haibo
, Maiti, Debabrata
, Mondal, Bhaskar
, Dajek, Maciej
in
119/118
/ 140/131
/ 140/58
/ 639/638/403/933
/ 639/638/549/933
/ 639/638/77/888
/ Alkenes
/ Bonding strength
/ Catalysis
/ Humanities and Social Sciences
/ Hydrocarbons
/ Hydrogen
/ Hydrogen bonding
/ Hydrogen bonds
/ Investigations
/ multidisciplinary
/ Nitrobenzene
/ Palladium
/ Regioselectivity
/ Science
/ Science (multidisciplinary)
/ Substrates
/ Urea
2024
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Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes
by
Kowalczyk, Rafal
, Dutta, Bishal
, Ghosh, Animesh
, Mahajan, Mayank
, Ge, Haibo
, Maiti, Debabrata
, Mondal, Bhaskar
, Dajek, Maciej
in
119/118
/ 140/131
/ 140/58
/ 639/638/403/933
/ 639/638/549/933
/ 639/638/77/888
/ Alkenes
/ Bonding strength
/ Catalysis
/ Humanities and Social Sciences
/ Hydrocarbons
/ Hydrogen
/ Hydrogen bonding
/ Hydrogen bonds
/ Investigations
/ multidisciplinary
/ Nitrobenzene
/ Palladium
/ Regioselectivity
/ Science
/ Science (multidisciplinary)
/ Substrates
/ Urea
2024
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Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes
Journal Article
Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes
2024
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Overview
Regioselective distal C−H functionalization of nitroarenes by overriding proximal C−H activation has remained an unsolved challenge. Herein, we present a palladium-catalyzed
meta
-C−H alkenylation of nitroarene substrate, achieved through leveraging the non-covalent hydrogen bonding interactions. Urea-based templates comprising an elongated biphenyl linker designed in such a way that it interacts with nitro group via strong hydrogen bonding interaction, while a cyano based directing group is attached along the template to coordinate with the palladium center, thereby facilitating the activation of the remote
meta
-C−H bond of nitrobenzene. Computational mechanistic investigation and the analysis of non-covalent interaction deciphers the crucial role of H-bonding in regulating the regioselectivity.
Regioselective distal C-H functionalization of nitroarenes by overriding proximal C-H activation has remained an unsolved challenge. Herein, the authors present a palladium-catalyzed meta-C-H alkenylation of nitroarene substrate, achieved through leveraging the noncovalent hydrogen bonding interactions.
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