Amide Effects in C-H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides.

Angew Chem Int Ed Engl

Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014, U.P., India.

Published: November 2018

AI Article Synopsis

  • A new method for the selective borylation of aromatic amides has been developed, showing that unlike esters which borylate at the para position, amides preferentially borylate at the meta position.
  • To achieve high selectivity for the meta position, researchers used an L-shaped bifunctional ligand that interacts with the oxygen of the amide's carbonyl group.
  • This unique interaction enhances the control needed for the meta C-H activation and borylation process.

Article 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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http://dx.doi.org/10.1002/anie.201809929DOI Listing

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