Literature DB >> 32385966

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

Han Seul Park1, Zhoulong Fan1, Ru-Yi Zhu1, Jin-Quan Yu1.   

Abstract

Reported herein is the distal γ-C(sp3 )-H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3 )-H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3 )-H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3 )-H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3 )-H olefinated products.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C(sp3)−H activation; amino acids; olefins; palladium; synthetic methods

Mesh：

Substances：

Year:  2020        PMID： 32385966      PMCID： PMC7494175          DOI： 10.1002/anie.202003271

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


  51 in total

1.  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

2.  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

3.  Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

Authors:  Ru-Yi Zhu; Keita Tanaka; Gen-Cheng Li; Jian He; Hai-Yan Fu; Su-Hua Li; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-05-27       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.  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

6.  Pd(II)-catalyzed olefination of sp3 C-H bonds.

Authors:  Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

7.  Direct β-C(sp3)-H Acetoxylation of Aliphatic Carboxylic Acids.

Authors:  Kiron K Ghosh; Alexander Uttry; Aylin Koldemir; Mike Ong; Manuel van Gemmeren
Journal:  Org Lett       Date:  2019-08-09       Impact factor: 6.005

8.  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

9.  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

10.  Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

Authors:  Ru-Yi Zhu; Jian He; Xiao-Chen Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2014-09-15       Impact factor: 15.419
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  7 in total

1.  PdII-Catalyzed Site-selective β- and γ-C(sp3)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

Authors:  Yi-Hao Li; Yuxin Ouyang; Nikita Chekshin; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2022-03-14       Impact factor: 16.383

2.  Ligand Enabled Pd(II)-Catalyzed γ-C(sp3)-H Lactamization of Native Amides.

Authors:  Shuang Liu; Zhe Zhuang; Jennifer X Qiao; Kap-Sun Yeung; Shun Su; Emily C Cherney; Zheming Ruan; William R Ewing; Michael A Poss; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2021-12-16       Impact factor: 16.383

3.  Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes.

Authors:  Ke Yang; Zhi Li; Chong Liu; Yunjian Li; Qingyue Hu; Mazen Elsaid; Bijin Li; Jayabrata Das; Yanfeng Dang; Debabrata Maiti; Haibo Ge
Journal:  Chem Sci       Date:  2022-04-25       Impact factor: 9.969

Review 4.  Pd-catalysed C-H functionalisation of free carboxylic acids.

Authors:  Suparna Dutta; Trisha Bhattacharya; Finn J Geffers; Marcel Bürger; Debabrata Maiti; Daniel B Werz
Journal:  Chem Sci       Date:  2022-01-10       Impact factor: 9.825

5.  A direct route to six and seven membered lactones via γ-C(sp3)-H activation: a simple protocol to build molecular complexity.

Authors:  Jayabrata Das; Pravas Dolui; Wajid Ali; Jyoti Prasad Biswas; Hediyala B Chandrashekar; Gaurav Prakash; Debabrata Maiti
Journal:  Chem Sci       Date:  2020-08-19       Impact factor: 9.825

Review 6.  Diverse strategies for transition metal catalyzed distal C(sp3)-H functionalizations.

Authors:  Jayabrata Das; Srimanta Guin; Debabrata Maiti
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

Review 7.  Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp3 )-H Bonds.

Authors:  Marc Font; Moisés Gulías; José Luis Mascareñas
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-02       Impact factor: 16.823
  7 in total

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