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Literature DB >> 30892775

Intermolecular, Branch-Selective, and Redox-Neutral Cp*Ir^III -Catalyzed Allylic C-H Amidation.

Tobias Knecht¹, Shobhan Mondal¹, Jian-Heng Ye¹, Mowpriya Das¹, Frank Glorius¹.

Abstract

Herein, we report the redox-neutral, intermolecular, and highly branch-selective amidation of allylic C-H bonds enabled by Cp*IrIII catalysis. A variety of readily available carboxylic acids were converted into the corresponding dioxazolones and efficiently coupled with terminal and internal olefins in high yields and selectivities. Mechanistic investigations support the formation of a nucleophilic IrIII -allyl intermediate rather than the direct insertion of an Ir-nitrenoid species into the allylic C-H bond.

Entities: Chemical

Keywords: C−H activation; allylic amidation; branch-selective reactions; carboxylic acids; redox-neutral reactions

Year: 2019 PMID： 30892775 DOI： 10.1002/anie.201901733

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. Cobalt(III)-Catalyzed C-H Amidation of Dehydroalanine for the Site-Selective Structural Diversification of Thiostrepton.

Authors: Ryan J Scamp; Edward deRamon; Eric K Paulson; Scott J Miller; Jonathan A Ellman
Journal: Angew Chem Int Ed Engl Date: 2019-11-27 Impact factor: 15.336

2. Late-Stage Intermolecular Allylic C-H Amination.

Authors: Takafumi Ide; Kaibo Feng; Charlie F Dixon; Dawei Teng; Joseph R Clark; Wei Han; Chloe I Wendell; Vanessa Koch; M Christina White
Journal: J Am Chem Soc Date: 2021-09-13 Impact factor: 15.419

3. Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex.

Authors: Finn Burg; Tomislav Rovis
Journal: J Am Chem Soc Date: 2021-10-20 Impact factor: 15.419

Review 4. C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.

Authors: Daniel S Brandes; Jonathan A Ellman
Journal: Chem Soc Rev Date: 2022-08-01 Impact factor: 60.615

Intermolecular, Branch-Selective, and Redox-Neutral Cp*Ir^III -Catalyzed Allylic C-H Amidation.

1. Cobalt(III)-Catalyzed C-H Amidation of Dehydroalanine for the Site-Selective Structural Diversification of Thiostrepton.

2. Late-Stage Intermolecular Allylic C-H Amination.

3. Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex.

Review 4. C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.

5. Allylic C-H amination cross-coupling furnishes tertiary amines by electrophilic metal catalysis.

Review 6. An Update of Transition Metal-Catalyzed Decarboxylative Transformations of Cyclic Carbonates and Carbamates.

7. Metal-free allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation.

8. Stereoretentive and regioselective selenium-catalyzed intermolecular propargylic C-H amination of alkynes.

Review 9. Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis.

10. Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes.