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Literature DB >> 23116159

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

Masayuki Wasa¹, Kelvin S L Chan, Xing-Guo Zhang, Jian He, Masanori Miura, Jin-Quan Yu.

Abstract

Pd(II) insertion into β-methylene C(sp(3))-H bonds was enabled by a mutually repulsive and electron-rich quinoline ligand. Ligand tuning led to the development of a method that allows for installation of an aryl group on a range of acyclic and cyclic amides containing β-methylene C(sp(3))-H bonds.

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Year: 2012 PMID： 23116159 PMCID： PMC3500088 DOI： 10.1021/ja309325e

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

33 in total

1. Pyridine ligands as promoters in Pd(II/0)-catalyzed C-H olefination reactions.

Authors: Asako Kubota; Marion H Emmert; Melanie S Sanford
Journal: Org Lett Date: 2012-03-12 Impact factor: 6.005

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. Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

Authors: Erika Milczek; Nadège Boudet; Simon Blakey
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

Authors: Rodolphe Jazzar; Julien Hitce; Alice Renaudat; Julien Sofack-Kreutzer; Olivier Baudoin
Journal: Chemistry Date: 2010-03-01 Impact factor: 5.236

5. Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.

Authors: Masayuki Wasa; Keary M Engle; David W Lin; Eun Jeong Yoo; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2011-11-21 Impact factor: 15.419

6. Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Authors: Chunhui Huang; Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2011-07-21 Impact factor: 15.419

7. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

Authors: Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal: Isr J Chem Date: 2010-12 Impact factor: 3.333

8. Sequential C(sp3)-H arylation and olefination: total synthesis of the proposed structure of pipercyclobutanamide A.

Authors: Will R Gutekunst; Ryan Gianatassio; Phil S Baran
Journal: Angew Chem Int Ed Engl Date: 2012-06-19 Impact factor: 15.336

9. Amide-Directed Arylation of sp C-H Bonds using Pd(II) and Pd(0) Catalysts.

Authors: Masayuki Wasa; Jin-Quan Yu
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

10. Palladium-catalyzed sp(3) CH activation of simple alkyl groups: direct preparation of indoline derivatives from N-alkyl-2-bromoanilines.

Authors: Toshiaki Watanabe; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal: Org Lett Date: 2008-04-08 Impact factor: 6.005

41 in total

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

Authors: Suhua Li; Ru-Yi Zhu; Kai-Jiong Xiao; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2016-02-25 Impact factor: 15.336

2. 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

3. A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Authors: Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal: Adv Synth Catal Date: 2014-01-13 Impact factor: 5.837

4. 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

5. Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

Authors: Jian He; Ryosuke Takise; Haiyan Fu; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-04-02 Impact factor: 15.419

Review 6. 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 methylene C(sp3)-H bond activation with a Pd(II) catalyst.

1. Pyridine ligands as promoters in Pd(II/0)-catalyzed C-H olefination reactions.

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

3. Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

4. Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

5. Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.

6. Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

7. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

8. Sequential C(sp3)-H arylation and olefination: total synthesis of the proposed structure of pipercyclobutanamide A.

9. Amide-Directed Arylation of sp C-H Bonds using Pd(II) and Pd(0) Catalysts.

10. Palladium-catalyzed sp(3) CH activation of simple alkyl groups: direct preparation of indoline derivatives from N-alkyl-2-bromoanilines.

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

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

3. A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

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

5. Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

Review 6. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

7. Highly Versatile β-C(sp³)-H Iodination of Ketones Using a Practical Auxiliary.

Review 8. A Simple and Versatile Amide Directing Group for C-H Functionalizations.

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

10. Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Review 6. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 8. A Simple and Versatile Amide Directing Group for C-H Functionalizations.

Review 6. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.