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Literature DB >> 32330054

Ligand-Enabled Pd(II)-Catalyzed C(sp³)-H Lactonization Using Molecular Oxygen as Oxidant.

Shaoqun Qian¹, Zi-Qi Li¹, Minyan Li¹, Steven R Wisniewski², Jennifer X Qiao³, Jeremy M Richter⁴, William R Ewing³, Martin D Eastgate², Jason S Chen⁵, Jin-Quan Yu¹.

Abstract

Pd(II)-catalyzed C-H lactonization of o-methyl benzoic acid substrates has been achieved using molecular oxygen as the oxidant. This finding provides a rare example of C-H oxygenation through Pd(II)/Pd(0) catalysis as well as a method to construct biologically important benzolactone scaffolds. The use of a gas mixture of 5% oxygen in nitrogen demonstrated the possibility for its application in pharmaceutical manufacturing.

Entities: Chemical Disease Gene Species

Year: 2020 PMID： 32330054 PMCID： PMC8023385 DOI： 10.1021/acs.orglett.0c01243

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

36 in total

1. Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Authors: Keary M Engle; Tian-Sheng Mei; Masayuki Wasa; Jin-Quan Yu
Journal: Acc Chem Res Date: 2011-12-14 Impact factor: 22.384

Review 2. Total synthesis of oxacyclic macrodiolide natural products.

Authors: Eun Joo Kang; Eun Lee
Journal: Chem Rev Date: 2005-12 Impact factor: 60.622

3. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

4. Ligand-accelerated enantioselective methylene C(sp3)-H bond activation.

Authors: Gang Chen; Wei Gong; Zhe Zhuang; Michal S Andrä; Yan-Qiao Chen; Xin Hong; Yun-Fang Yang; Tao Liu; K N Houk; Jin-Quan Yu
Journal: Science Date: 2016-09-02 Impact factor: 47.728

5. Green, catalytic oxidation of alcohols in water

Authors:
Journal: Science Date: 2000-03-03 Impact factor: 47.728

6. Combined C-H functionalization/C-N bond formation route to carbazoles.

Authors: W C Peter Tsang; Nan Zheng; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-10-26 Impact factor: 15.419

Review 7. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors: Keary M Engle; Jin-Quan Yu
Journal: J Org Chem Date: 2013-05-03 Impact factor: 4.354

8. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

Authors: Masayuki Wasa; Kelvin S L Chan; Xing-Guo Zhang; Jian He; Masanori Miura; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2012-11-05 Impact factor: 15.419

Review 9. 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

10. GABA_A receptor signalling mechanisms revealed by structural pharmacology.

Authors: Simonas Masiulis; Rooma Desai; Tomasz Uchański; Itziar Serna Martin; Duncan Laverty; Dimple Karia; Tomas Malinauskas; Jasenko Zivanov; Els Pardon; Abhay Kotecha; Jan Steyaert; Keith W Miller; A Radu Aricescu
Journal: Nature Date: 2019-01-02 Impact factor: 49.962

4 in total

Ligand-Enabled Pd(II)-Catalyzed C(sp³)-H Lactonization Using Molecular Oxygen as Oxidant.

1. Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Review 2. Total synthesis of oxacyclic macrodiolide natural products.

3. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

4. Ligand-accelerated enantioselective methylene C(sp3)-H bond activation.

5. Green, catalytic oxidation of alcohols in water

6. Combined C-H functionalization/C-N bond formation route to carbazoles.

Review 7. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

8. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

Review 9. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

10. GABA_A receptor signalling mechanisms revealed by structural pharmacology.

Review 1. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

2. Unconventional mechanism and selectivity of the Pd-catalyzed C-H bond lactonization in aromatic carboxylic acid.

Review 3. Pd-catalysed C-H functionalisation of free carboxylic acids.

Review 4. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp³ )-H Bonds.

Review 2. Total synthesis of oxacyclic macrodiolide natural products.

Review 7. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Review 9. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Review 1. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 3. Pd-catalysed C-H functionalisation of free carboxylic acids.

Review 4. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp3 )-H Bonds.

Review 1. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Review 4. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp³ )-H Bonds.