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Literature DB >> 28707312

Selective Palladium(II)-Catalyzed Carbonylation of Methylene β-C-H Bonds in Aliphatic Amines.

Jaime R Cabrera-Pardo¹, Aaron Trowbridge¹, Manuel Nappi¹, Kyohei Ozaki¹, Matthew J Gaunt¹.

Abstract

Palladium(II)-catalyzed C-H carbonylation reactions of methylene C-H bonds in secondary aliphatic amines lead to the formation of trans-disubstituted β-lactams in excellent yields and selectivities. The generality of the C-H carbonylation process is aided by the action of xantphos-based ligands and is important in securing good yields for the β-lactam products.

Entities: Chemical

Keywords: C−H activation; aliphatic amines; carbonylation; lactams; palladium catalysis

Year: 2017 PMID： 28707312 DOI： 10.1002/anie.201706303

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

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Cited

10 in total

1. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

Authors: Pablo J Cabrera; Melissa Lee; Melanie S Sanford
Journal: J Am Chem Soc Date: 2018-04-13 Impact factor: 15.419

2. Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.

Authors: Caleb Karmel; Bijie Li; John F Hartwig
Journal: J Am Chem Soc Date: 2018-01-22 Impact factor: 15.419

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Authors: Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal: Chem Rev Date: 2021-10-29 Impact factor: 60.622

4. 1-Aminopyridinium Ylides as Monodentate Directing Groups for sp³ C-H Bond Functionalization.

Authors: Ky Khac Anh Le; Hanh Nguyen; Olafs Daugulis
Journal: J Am Chem Soc Date: 2019-09-06 Impact factor: 15.419

Review 5. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors: Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal: Chem Soc Rev Date: 2018-08-28 Impact factor: 54.564

Selective Palladium(II)-Catalyzed Carbonylation of Methylene β-C-H Bonds in Aliphatic Amines.

1. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

2. Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

4. 1-Aminopyridinium Ylides as Monodentate Directing Groups for sp³ C-H Bond Functionalization.

Review 5. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Review 6. sp³ C-H activation via exo-type directing groups.

7. The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C-H bonds.

8. Diastereoselective C-H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams.

9. Ligand-Enabled β-C(sp³ )-H Lactamization of Tosyl-Protected Aliphatic Amides Using a Practical Oxidant.

Review 10. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp³ )-H Bonds.

Selective Palladium(II)-Catalyzed Carbonylation of Methylene β-C-H Bonds in Aliphatic Amines.

1. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

2. Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

4. 1-Aminopyridinium Ylides as Monodentate Directing Groups for sp3 C-H Bond Functionalization.

Review 5. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Review 6. sp3 C-H activation via exo-type directing groups.

7. The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C-H bonds.

8. Diastereoselective C-H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams.

9. Ligand-Enabled β-C(sp3 )-H Lactamization of Tosyl-Protected Aliphatic Amides Using a Practical Oxidant.

Review 10. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp3 )-H Bonds.

Review 3. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

4. 1-Aminopyridinium Ylides as Monodentate Directing Groups for sp³ C-H Bond Functionalization.

Review 6. sp³ C-H activation via exo-type directing groups.

9. Ligand-Enabled β-C(sp³ )-H Lactamization of Tosyl-Protected Aliphatic Amides Using a Practical Oxidant.

Review 10. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp³ )-H Bonds.