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Imine as a linchpin approach for meta-C–H functionalization
by
Goswami, Nupur
, Bag, Sukdev
, Bhowmick, Suman
, Maiti, Debabrata
, Jana, Sadhan
, Sinha, Soumya Kumar
, Pradhan, Sukumar
in
639/638/403/933
/ 639/638/77/885
/ 639/638/77/888
/ Binding sites
/ Chemical synthesis
/ Covalent bonds
/ Design
/ Fluorine
/ Geometry
/ Humanities and Social Sciences
/ Hydrogen bonds
/ Ligands
/ Molecular weight
/ multidisciplinary
/ Organic chemistry
/ Science
/ Science (multidisciplinary)
/ Selectivity
/ Streamlining
2021
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Imine as a linchpin approach for meta-C–H functionalization
by
Goswami, Nupur
, Bag, Sukdev
, Bhowmick, Suman
, Maiti, Debabrata
, Jana, Sadhan
, Sinha, Soumya Kumar
, Pradhan, Sukumar
in
639/638/403/933
/ 639/638/77/885
/ 639/638/77/888
/ Binding sites
/ Chemical synthesis
/ Covalent bonds
/ Design
/ Fluorine
/ Geometry
/ Humanities and Social Sciences
/ Hydrogen bonds
/ Ligands
/ Molecular weight
/ multidisciplinary
/ Organic chemistry
/ Science
/ Science (multidisciplinary)
/ Selectivity
/ Streamlining
2021
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Do you wish to request the book?
Imine as a linchpin approach for meta-C–H functionalization
by
Goswami, Nupur
, Bag, Sukdev
, Bhowmick, Suman
, Maiti, Debabrata
, Jana, Sadhan
, Sinha, Soumya Kumar
, Pradhan, Sukumar
in
639/638/403/933
/ 639/638/77/885
/ 639/638/77/888
/ Binding sites
/ Chemical synthesis
/ Covalent bonds
/ Design
/ Fluorine
/ Geometry
/ Humanities and Social Sciences
/ Hydrogen bonds
/ Ligands
/ Molecular weight
/ multidisciplinary
/ Organic chemistry
/ Science
/ Science (multidisciplinary)
/ Selectivity
/ Streamlining
2021
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Imine as a linchpin approach for meta-C–H functionalization
Journal Article
Imine as a linchpin approach for meta-C–H functionalization
2021
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Overview
Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing groups (DGs) served as ancillary ligands to ensure
ortho
-,
meta
- and
para
-C–H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. Here we report a temporary directing group (TDG) for
meta
-C–H functionalization via reversible imine formation. By overruling facile
ortho
-C–H bond activation by imine-
N
atom, a suitably designed pyrimidine-based TDG successfully delivered selective
meta
-C–C bond formation. Application of this temporary directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the
meta
position has been explored.
Site-selective C–H functionalization still faces some challenges, such as the introduction and removal of an appropriate directing group. Here, the authors introduce a temporary directing group for selective
meta
-C–H functionalization of 2-arylbenzaldehydes via reversible imine formation.
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