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Literature DB >> 29086554

Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp³)-H Activation.

Ru-Yi Zhu¹, Luo-Yan Liu¹, Han Seul Park¹, Kai Hong¹, Yongwei Wu¹, Chris H Senanayake², Jin-Quan Yu¹.

Abstract

We report Pd(II)-catalyzed β-C(sp3)-H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported β-C(sp3)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl coupling involving both primary and secondary alkyls.

Entities: Chemical Disease Species

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Year: 2017 PMID： 29086554 PMCID： PMC5710734 DOI： 10.1021/jacs.7b09761

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

20 in total

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Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

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Authors: Valery M Dembitsky
Journal: J Nat Med Date: 2007-09-05 Impact factor: 2.343

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Authors: Edward M Driggers; Stephen P Hale; Jinbo Lee; Nicholas K Terrett
Journal: Nat Rev Drug Discov Date: 2008-07 Impact factor: 84.694

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

Authors: Ru-Yi Zhu; Luo-Yan Liu; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2017-08-29 Impact factor: 15.419

5. Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

Authors: Hung-Yat Thu; Wing-Yiu Yu; Chi-Ming Che
Journal: J Am Chem Soc Date: 2006-07-19 Impact factor: 15.419

6. A monoterpene alkaloid from incarvillea sinensis.

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Journal: Chem Pharm Bull (Tokyo) Date: 2005-09 Impact factor: 1.645

7. Methylene C(sp³)-H Arylation of Aliphatic Ketones Using a Transient Directing Group.

Authors: Kai Hong; Hojoon Park; Jin-Quan Yu
Journal: ACS Catal Date: 2017-09-13 Impact factor: 13.084

8. Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group.

Authors: Fang-Lin Zhang; Kai Hong; Tuan-Jie Li; Hojoon Park; Jin-Quan Yu
Journal: Science Date: 2016-01-15 Impact factor: 47.728

Review 9. Macrocycles in new drug discovery.

Authors: Jamie Mallinson; Ian Collins
Journal: Future Med Chem Date: 2012-07 Impact factor: 3.808

10. Single-Electron Transmetalation via Photoredox/Nickel Dual Catalysis: Unlocking a New Paradigm for sp(3)-sp(2) Cross-Coupling.

Authors: John C Tellis; Christopher B Kelly; David N Primer; Matthieu Jouffroy; Niki R Patel; Gary A Molander
Journal: Acc Chem Res Date: 2016-07-05 Impact factor: 22.384

5 in total

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

Authors: Han Seul Park; Zhoulong Fan; Ru-Yi Zhu; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2020-06-05 Impact factor: 15.336

2. Ligand-Enabled β-Methylene C(sp³ )-H Arylation of Masked Aliphatic Alcohols.

Authors: Guoqin Xia; Zhe Zhuang; Luo-Yan Liu; Stuart L Schreiber; Bruno Melillo; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2020-03-11 Impact factor: 15.336

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

Authors: Ru-Yi Zhu; Zi-Qi Li; Han Seul Park; Chris H Senanayake; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2018-03-02 Impact factor: 15.419

5. Merging C(sp³)-H activation with DNA-encoding.

Authors: Zhoulong Fan; Shuai Zhao; Tao Liu; Peng-Xiang Shen; Zi-Ning Cui; Zhe Zhuang; Qian Shao; Jason S Chen; Anokha S Ratnayake; Mark E Flanagan; Dominik K Kölmel; David W Piotrowski; Paul Richardson; Jin-Quan Yu
Journal: Chem Sci Date: 2020-09-07 Impact factor: 9.825