Amide Effects in C−H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides
Ranjana Bisht
Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India
These authors contributed equally to this work.
Search for more papers by this authorMd Emdadul Hoque
Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Buddhadeb Chattopadhyay
Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India
Search for more papers by this authorRanjana Bisht
Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India
These authors contributed equally to this work.
Search for more papers by this authorMd Emdadul Hoque
Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Buddhadeb Chattopadhyay
Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India
Search for more papers by this authorGraphical Abstract
L-Shaped: A new concept for the meta borylation of aromatic amides is described. It has been shown that while esters give para borylations, amides result in meta borylations. For achieving high meta selectivity, an L-shaped ligand is used and engages in an O⋅⋅⋅K noncovalent interaction with the moderately distorted amide carbonyl group, providing 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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