Amide Effects in C−H Activation: Noncovalent Interactions with L‐Shaped Ligand for meta Borylation of Aromatic Amides
Angewandte Chemie International Edition, 2018•Wiley Online Library
A new concept for the meta‐selective borylation of aromatic amides is described. It has been
demonstrated that while esters gave para borylations, amides lead to meta borylations. For
achieving high meta selectivity, an L‐shaped bifunctional ligand has been employed and
engages in an O⋅⋅⋅ K noncovalent interaction with the oxygen atom of the moderately
distorted amide carbonyl group. This interaction provides exceptional control for meta C− H
activation/borylation.
demonstrated that while esters gave para borylations, amides lead to meta borylations. For
achieving high meta selectivity, an L‐shaped bifunctional ligand has been employed and
engages in an O⋅⋅⋅ K noncovalent interaction with the oxygen atom of the moderately
distorted amide carbonyl group. This interaction provides exceptional control for meta C− H
activation/borylation.
Abstract
A new concept for the meta‐selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L‐shaped bifunctional ligand has been employed and engages in an O⋅⋅⋅K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C−H activation/borylation.
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