Literature DB >> 20593075

Selectivity enhancement in functionalization of C-H bonds: A review.

Georgiy B Shul'pin1.   

Abstract

The selectivity is an extremely important characteristic of a chemical reaction. This review deals mainly with supramolecular and nano-chemical approaches to the problem of selectivity enhancement in various functionalizations of C-H compounds. Enzyme mimics is a very fruitful method to achieve the predominant formation of desirable products and isomers. By obstructing the approach of certain C-H bonds of a substrate to the active catalytic centre we simultaneously increase the relative reactivity of other fragments. This can be done by creating steric hindrance around the active centre. Spatial restrictions can be made if we place the catalyst into a nano-cavity. We can achieve discrimination in reactivity of different C-H bonds if we allow certain fragments to approach closely the active centre. In order to do this chemists use coordination of the catalyst to some groups of the substrate with the participation of relatively strong binding (chelate control) or relatively weak forces (molecular recognition).

Entities:  

Year:  2010        PMID: 20593075     DOI: 10.1039/c004223d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  11 in total

1.  Transition State Asymmetry in C-H Bond Cleavage by Proton-Coupled Electron Transfer.

Authors:  Julia W Darcy; Scott S Kolmar; James M Mayer
Journal:  J Am Chem Soc       Date:  2019-06-27       Impact factor: 15.419

Review 2.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

3.  Inverting Steric Effects: Using "Attractive" Noncovalent Interactions To Direct Silver-Catalyzed Nitrene Transfer.

Authors:  Minxue Huang; Tzuhsiung Yang; Jonathan D Paretsky; John F Berry; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419

Review 4.  Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Chem Rev       Date:  2017-06-05       Impact factor: 60.622

5.  Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.

Authors:  Anton V Gulevich; Ferdinand S Melkonyan; Dhruba Sarkar; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2012-03-19       Impact factor: 15.419

6.  Enhanced reactivity in dioxirane C-H oxidations via strain release: a computational and experimental study.

Authors:  Lufeng Zou; Robert S Paton; Albert Eschenmoser; Timothy R Newhouse; Phil S Baran; K N Houk
Journal:  J Org Chem       Date:  2013-03-22       Impact factor: 4.354

7.  Carboxylate-assisted C-H activation of phenylpyridines with copper, palladium and ruthenium: a mass spectrometry and DFT study.

Authors:  A Gray; A Tsybizova; J Roithova
Journal:  Chem Sci       Date:  2015-07-01       Impact factor: 9.825

8.  Mechanistic Study of Copper-Catalyzed C-H Hydroxylation/C-S Coupling by ESI-HR MS and DFT Calculations.

Authors:  Runsheng Xu; Rongrong Cai; Sixian Zhou; Zhuoda Zhou; Beibei Li; Dihui Xu
Journal:  Molecules       Date:  2017-11-06       Impact factor: 4.411

Review 9.  Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization.

Authors:  A Sofia Santos; Ana C Mortinho; M Manuel B Marques
Journal:  Molecules       Date:  2018-10-17       Impact factor: 4.411

10.  Peroxidative Oxidation of Alkanes and Alcohols under Mild Conditions by Di- and Tetranuclear Copper (II) Complexes of Bis (2-Hydroxybenzylidene) Isophthalohydrazide.

Authors:  Manas Sutradhar; Elisabete C B A Alegria; M Fátima C Guedes da Silva; Cai-Ming Liu; Armando J L Pombeiro
Journal:  Molecules       Date:  2018-10-19       Impact factor: 4.411

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