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Literature DB >> 26919066

Ligand-Enabled Arylation of γ-C-H Bonds.

Suhua Li¹, Ru-Yi Zhu¹, Kai-Jiong Xiao¹, Jin-Quan Yu².

Abstract

Pd(II) -catalyzed arylation of γ-C(sp(3) )-H bonds of aliphatic acid-derived amides was developed by using quinoline-based ligands. Various γ-aryl-α-amino acids were prepared from natural amino acids using this method. The influence of ligand structure on reactivity was also systematically investigated.

Entities: Chemical Species

Keywords: arylation; carboxylic acids; palladium; quinoline ligand; γ-C-H activation

Mesh：

Substances：

Year: 2016 PMID： 26919066 PMCID： PMC4821162 DOI： 10.1002/anie.201512020

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

50 in total

1. Selective functionalization of amino acids in water: a synthetic method via catalytic C-H bond activation.

Authors: B D Dangel; J A Johnson; D Sames
Journal: J Am Chem Soc Date: 2001-08-22 Impact factor: 15.419

2. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

3. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Authors: Ramesh Giri; Xiao Chen; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2005-03-29 Impact factor: 15.336

4. Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: a dual role for carboxylic anhydrides in catalytic C--H bond oxidation.

Authors: Ramesh Giri; Jue Liang; Jian-Guang Lei; Jiao-Jie Li; Dong-Hui Wang; Xiao Chen; Isaac Clement Naggar; Chengyun Guo; Bruce M Foxman; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2005-12-01 Impact factor: 15.336

5. 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

6. 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

7. Palladium-catalyzed methylation and arylation of sp2 and sp3 C-H bonds in simple carboxylic acids.

Authors: Ramesh Giri; Nathan Maugel; Jiao-Jie Li; Dong-Hui Wang; Steven P Breazzano; Lindsey B Saunders; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2007-03-03 Impact factor: 15.419

8. Strong conformational preferences of heteroaromatic ethers and electron pair repulsion.

Authors: Rong-Jie Chein; E J Corey
Journal: Org Lett Date: 2010-01-01 Impact factor: 6.005

9. 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

10. Pd(II)-catalyzed cross-coupling of sp3 C-H Bonds with sp2 and sp3 boronic acids using air as the oxidant.

Authors: Dong-Hui Wang; Masayuki Wasa; Ramesh Giri; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2008-05-14 Impact factor: 15.419

18 in total

1. 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

Review 2. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

Ligand-Enabled Arylation of γ-C-H Bonds.

1. Selective functionalization of amino acids in water: a synthetic method via catalytic C-H bond activation.

2. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

3. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

4. Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: a dual role for carboxylic anhydrides in catalytic C--H bond oxidation.

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

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

7. Palladium-catalyzed methylation and arylation of sp2 and sp3 C-H bonds in simple carboxylic acids.

8. Strong conformational preferences of heteroaromatic ethers and electron pair repulsion.

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

10. Pd(II)-catalyzed cross-coupling of sp3 C-H Bonds with sp2 and sp3 boronic acids using air as the oxidant.

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

Review 2. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

3. Distal γ-C(sp³ )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

4. Ligand-Enabled β-C-H Arylation of α-Amino Acids Without Installing Exogenous Directing Groups.

5. Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.

6. Ligand-Enabled γ-C(sp³)-H Activation of Ketones.

7. Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.

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

9. Rational Development of Remote C-H Functionalization of Biphenyl: Experimental and Computational Studies.

10. Directed γ-C(sp³)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis.

Review 2. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 2. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.