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Literature DB >> 30306677

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

Ranjana Bisht¹, Md Emdadul Hoque¹, Buddhadeb Chattopadhyay¹.

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.

Entities: Chemical

Keywords: C−H activation; amides; borylation; iridium; noncovalent interactions

Year: 2018 PMID： 30306677 DOI： 10.1002/anie.201809929

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

11 in total

1. Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis.

Authors: Caleb Karmel; Zhewei Chen; John F Hartwig
Journal: J Am Chem Soc Date: 2019-04-23 Impact factor: 15.419

Review 2. Achieving Site-Selectivity for C-H Activation Processes Based on Distance and Geometry: A Carpenter's Approach.

Authors: Guangrong Meng; Nelson Y S Lam; Erika L Lucas; Tyler G Saint-Denis; Pritha Verma; Nikita Chekshin; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2020-06-05 Impact factor: 15.419

Review 3. Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds.

Authors: James E Gillespie; Alexander Fanourakis; Robert J Phipps
Journal: J Am Chem Soc Date: 2022-09-30 Impact factor: 16.383

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

1. Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis.

Review 2. Achieving Site-Selectivity for C-H Activation Processes Based on Distance and Geometry: A Carpenter's Approach.

Review 3. Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds.

Review 4. Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.

5. Hydrogen Bond Directed ortho-Selective C-H Borylation of Secondary Aromatic Amides.

Review 6. Indolylboronic Acids: Preparation and Applications.

7. Ion-Pair-Directed Borylation of Aromatic Phosphonium Salts.

Review 8. Site-Selective C-H Functionalization of Arenes Enabled by Noncovalent Interactions.

9. Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation.

10. Recyclable Ruthenium Catalyst for Distal meta-C-H Activation.