Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Palladium-Catalyzed Pyrazole-Directed sp3 C-H Bond Arylation for the Synthesis of β-Phenethylamines.

Literature DB >> 28233918

Palladium-Catalyzed Pyrazole-Directed sp³ C-H Bond Arylation for the Synthesis of β-Phenethylamines.

Abstract

We have developed a method for palladium-catalyzed, pyrazole-directed sp3 C-H bond arylation by aryl iodides. The reaction employs a Pd(OAc)2 catalyst at 5-10 mol % loading and silver(I) oxide as a halide-removal agent, and it proceeds in acetic acid or acetic acid/hexafluoroisopropanol solvent. Ozonolysis of the pyrazole moiety affords pharmaceutically important β-phenethylamines.

Entities: Chemical Gene

Keywords: C−C coupling; C−H activation; arenes; homogeneous catalysis; palladium

Mesh：

Substances：

Year: 2017 PMID： 28233918 PMCID： PMC5480374 DOI： 10.1002/anie.201611407

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

54 in total

1. Highly regioselective arylation of sp3 C-H bonds catalyzed by palladium acetate.

Authors: Vladimir G Zaitsev; Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2005-09-28 Impact factor: 15.419

2. Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

Authors: B V Subba Reddy; Leleti Rajender Reddy; E J Corey
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

3. Catalytic coupling of C-H and C-I bonds using pyridine as a directing group.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: Org Lett Date: 2005-08-18 Impact factor: 6.005

4. Catalytic arylation reactions by C-H bond activation with aryl tosylates.

Authors: Lutz Ackermann; Andreas Althammer; Robert Born
Journal: Angew Chem Int Ed Engl Date: 2006-04-10 Impact factor: 15.336

5. Catalytic and highly regioselective cross-coupling of aromatic C-H substrates.

Authors: Kami L Hull; Melanie S Sanford
Journal: J Am Chem Soc Date: 2007-09-11 Impact factor: 15.419

Review 6. A renaissance in trace amines inspired by a novel GPCR family.

Authors: Lothar Lindemann; Marius C Hoener
Journal: Trends Pharmacol Sci Date: 2005-05 Impact factor: 14.819

7. Oxaziridine-mediated amination of primary amines: scope and application to a one-pot pyrazole synthesis.

Authors: Alan Armstrong; Lyn H Jones; Jamie D Knight; Richard D Kelsey
Journal: Org Lett Date: 2005-02-17 Impact factor: 6.005

8. Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds.

Authors: Lopa V Desai; Kami L Hull; Melanie S Sanford
Journal: J Am Chem Soc Date: 2004-08-11 Impact factor: 15.419

Review 9. The vascular effects of trace amines and amphetamines.

Authors: Kenneth J Broadley
Journal: Pharmacol Ther Date: 2009-12-04 Impact factor: 12.310

Review 10. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

Authors: Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

7 in total

1. Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium-Catalyzed C-H Bond Functionalization Methodology.

Authors: Se Hun Kwak; Nurbey Gulia; Olafs Daugulis
Journal: J Org Chem Date: 2018-05-08 Impact factor: 4.354

Review 2. 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

3. 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 4. 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

Palladium-Catalyzed Pyrazole-Directed sp³ C-H Bond Arylation for the Synthesis of β-Phenethylamines.

1. Highly regioselective arylation of sp3 C-H bonds catalyzed by palladium acetate.

2. Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

3. Catalytic coupling of C-H and C-I bonds using pyridine as a directing group.

4. Catalytic arylation reactions by C-H bond activation with aryl tosylates.

5. Catalytic and highly regioselective cross-coupling of aromatic C-H substrates.

Review 6. A renaissance in trace amines inspired by a novel GPCR family.

7. Oxaziridine-mediated amination of primary amines: scope and application to a one-pot pyrazole synthesis.

8. Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds.

Review 9. The vascular effects of trace amines and amphetamines.

Review 10. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

1. Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium-Catalyzed C-H Bond Functionalization Methodology.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

3. 1-Aminopyridinium Ylides as Monodentate Directing Groups for sp³ C-H Bond Functionalization.

Review 4. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

5. Site-Selective Pd-Catalyzed C(sp³ )-H Arylation of Heteroaromatic Ketones.

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.

Review 6. A renaissance in trace amines inspired by a novel GPCR family.

Review 9. The vascular effects of trace amines and amphetamines.

Review 10. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 4. 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.

Review 2. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

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