Literature DB >> 35951267

Metal-Free Catalysis in C-C Single-Bond Cleavage: Achievements and Prospects.

Mohit L Deb1, B Shriya Saikia2, Iftakur Rahman2, Pranjal Kumar Baruah3.   

Abstract

This review article emphasizes the C-C bond cleavage in organic synthesis via metal-free approach. Conventional organic synthesis mainly deals with the reactive π bonds and polar σ bonds. In contrast, the ubiquitous C-C single bonds are inherently stable and are less reactive, which poses a challenge to synthetic chemists. Although inert, such C-C single-bond cleavage reactions have gained attention amongst synthetic chemists, as they provide unique and more straightforward routes, with significantly fewer steps. Several review articles have been reported regarding the activation and cleavage of C-C bonds using different transition metals. However, given the high cost and toxicity of many of these metals, the development of strategies under metal-free conditions is of utmost importance. Though many research articles have been published in this area, no review article has been reported so far. Herein, we discuss the reactions in a more concise way from the year 2012 to today, with emphasis on important reactions. Mechanisms of all the reactions are also well addressed. We believe that this review will be beneficial for the readers who work in this field.
© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

Entities:  

Keywords:  Carbonyls; C–C bond cleavage; Inert bond; Metal-free; Ring strain; Synthetic methods

Mesh:

Substances:

Year:  2022        PMID: 35951267     DOI: 10.1007/s41061-022-00393-7

Source DB:  PubMed          Journal:  Top Curr Chem (Cham)        ISSN: 2364-8961


  38 in total

1.  Mn-promoted aerobic oxidative C-C bond cleavage of aldehydes with dioxygen activation: a simple synthetic approach to formamides.

Authors:  Chun Zhang; Zejun Xu; Tao Shen; Guolin Wu; Liangren Zhang; Ning Jiao
Journal:  Org Lett       Date:  2012-04-26       Impact factor: 6.005

Review 2.  A review of mechanistic studies on aromatase (CYP19) and 17α-hydroxylase-17,20-lyase (CYP17).

Authors:  Muhammad Akhtar; J Neville Wright; Peter Lee-Robichaud
Journal:  J Steroid Biochem Mol Biol       Date:  2010-11-19       Impact factor: 4.292

3.  From ketones to esters by a Cu-catalyzed highly selective C(CO)-C(alkyl) bond cleavage: aerobic oxidation and oxygenation with air.

Authors:  Xiaoqiang Huang; Xinyao Li; Miancheng Zou; Song Song; Conghui Tang; Yizhi Yuan; Ning Jiao
Journal:  J Am Chem Soc       Date:  2014-10-07       Impact factor: 15.419

4.  Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage.

Authors:  Wenyou Fan; Youqing Yang; Jianhua Lei; Qijian Jiang; Wang Zhou
Journal:  J Org Chem       Date:  2015-08-26       Impact factor: 4.354

5.  A one-pot copper catalyzed biomimetic route to N-heterocyclic amides from methyl ketones via oxidative C-C bond cleavage.

Authors:  Parthasarathi Subramanian; Satrajit Indu; Krishna P Kaliappan
Journal:  Org Lett       Date:  2014-11-19       Impact factor: 6.005

6.  Intramolecular Cooperative C-C Bond Cleavage Reaction of 1,3-Dicarbonyl Compounds with 2-Iodoanilines to Give o-(N-Acylamino)aryl Ketones and Multisubstituted Indoles.

Authors:  Qi Xing; Hui Lv; Chungu Xia; Fuwei Li
Journal:  Chemistry       Date:  2015-05-04       Impact factor: 5.236

7.  Organic chemistry. Rh-catalyzed C-C bond cleavage by transfer hydroformylation.

Authors:  Stephen K Murphy; Jung-Woo Park; Faben A Cruz; Vy M Dong
Journal:  Science       Date:  2015-01-02       Impact factor: 47.728

8.  Copper-catalyzed aerobic oxidative C-C bond cleavage of unstrained ketones with air and amines.

Authors:  Wang Zhou; Wenyou Fan; Qijian Jiang; Yu-Feng Liang; Ning Jiao
Journal:  Org Lett       Date:  2015-05-07       Impact factor: 6.005

9.  N-acyl DBN tetraphenylborate salts as N-acylating agents.

Authors:  James E Taylor; Matthew D Jones; Jonathan M J Williams; Steven D Bull
Journal:  J Org Chem       Date:  2012-02-28       Impact factor: 4.354

Review 10.  The diverse chemistry of cytochrome P450 17A1 (P450c17, CYP17A1).

Authors:  Francis K Yoshimoto; Richard J Auchus
Journal:  J Steroid Biochem Mol Biol       Date:  2014-12-04       Impact factor: 4.292

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