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Literature DB >> 29481072

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

Ru-Yi Zhu¹, Zi-Qi Li¹, Han Seul Park¹, Chris H Senanayake², Jin-Quan Yu¹.

Abstract

We report the first example of Pd(II)-catalyzed γ-C(sp3)-H activation of ketones directed by a practical 2,2-dimethyl aminooxyacetic acid auxiliary. 2-Pyridone ligands are identified to enable C(sp3)-H activation for the first time. A rare six-membered palladacycle intermediate is isolated and characterized to elucidate the reaction mechanism. Both (hetero)arylation and vinylation of γ-C(sp3)-H bonds are demonstrated. Sequential β- and γ-C(sp3)-H (hetero)arylation of muscone showcases the utility of this method for late-stage diversification. A convenient Mn(II)-catalyzed auxiliary removal is also developed to further underscore the practicality of this transformation.

Entities: Chemical Species

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Year: 2018 PMID： 29481072 PMCID： PMC5851877 DOI： 10.1021/jacs.8b01359

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

33 in total

1. 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

2. Palladium-catalyzed direct functionalization of 2-aminobutanoic acid derivatives: application of a convenient and versatile auxiliary.

Authors: Mengyang Fan; Dawei Ma
Journal: Angew Chem Int Ed Engl Date: 2013-09-23 Impact factor: 15.336

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

Authors: Ru-Yi Zhu; Luo-Yan Liu; Han Seul Park; Kai Hong; Yongwei Wu; Chris H Senanayake; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2017-11-03 Impact factor: 15.419

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. 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

6. 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

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. α-Aminoxy-Acid-Auxiliary-Enabled Intermolecular Radical γ-C(sp³ )-H Functionalization of Ketones.

Authors: Heng Jiang; Armido Studer
Journal: Angew Chem Int Ed Engl Date: 2018-01-15 Impact factor: 15.336

9. Palladium catalyzed direct aliphatic γC(sp³)-H alkenylation with alkenes and alkenyl iodides.

Authors: Neetipalli Thrimurtulu; Salman Khan; Soham Maity; Chandra M R Volla; Debabrata Maiti
Journal: Chem Commun (Camb) Date: 2017-11-16 Impact factor: 6.222

10. Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.

Authors: Elizabeth M Dauncey; Sara P Morcillo; James J Douglas; Nadeem S Sheikh; Daniele Leonori
Journal: Angew Chem Int Ed Engl Date: 2017-12-04 Impact factor: 15.336

19 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

3. Reversing conventional site-selectivity in C(sp³)-H bond activation.

Authors: Guoqin Xia; Jiang Weng; Luoyan Liu; Pritha Verma; Ziqi Li; Jin-Quan Yu
Journal: Nat Chem Date: 2019-04-15 Impact factor: 24.427

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

Authors: Laura K G Ackerman; Jesus I Martinez Alvarado; Abigail G Doyle
Journal: J Am Chem Soc Date: 2018-10-16 Impact factor: 15.419

5. Pd^II -Catalyzed Enantioselective C(sp³ )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

Authors: Li-Jun Xiao; Kai Hong; Fan Luo; Liang Hu; William R Ewing; Kap-Sun Yeung; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2020-04-01 Impact factor: 15.336

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

Authors: Shaoqun Qian; Zi-Qi Li; Minyan Li; Steven R Wisniewski; Jennifer X Qiao; Jeremy M Richter; William R Ewing; Martin D Eastgate; Jason S Chen; Jin-Quan Yu
Journal: Org Lett Date: 2020-04-24 Impact factor: 6.005

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

Authors: Zhoulong Fan; Katherine L Bay; Xiangyang Chen; Zhe Zhuang; Han Seul Park; Kap-Sun Yeung; K N Houk; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2020-02-12 Impact factor: 15.336

8. Diversity-oriented functionalization of 2-pyridones and uracils.

Authors: Yong Shang; Chenggui Wu; Qianwen Gao; Chang Liu; Lisha Li; Xinping Zhang; Hong-Gang Cheng; Shanshan Liu; Qianghui Zhou
Journal: Nat Commun Date: 2021-05-20 Impact factor: 14.919

9. 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

10. Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.

Authors: Yu-Jie Wang; Chen-Hui Yuan; De-Zhao Chu; Lei Jiao
Journal: Chem Sci Date: 2020-09-23 Impact factor: 9.825