Literature DB >> 21344074

The frequently overlooked importance of solvent in free radical syntheses.

Grzegorz Litwinienko1, A L J Beckwith, K U Ingold.   

Abstract

This tutorial review is designed to dispel the myth, still believed by many synthetic organic chemists, that radical-based syntheses are free from significant solvent effects. However, many synthetically valuable radical reactions do exhibit large kinetic solvent effects. It is therefore important to select the solvent for any proposed radical synthesis with considerable care if good product yields are to be achieved.

Entities:  

Year:  2011        PMID: 21344074     DOI: 10.1039/c1cs15007c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  6 in total

1.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

2.  Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations.

Authors:  Jennifer L Stockdill; Alberto M Lopez; Ahmad A Ibrahim
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  γ C-H Functionalization of Amines via Triple H-Atom Transfer of a Vinyl Sulfonyl Radical Chaperone.

Authors:  James H Herbort; Taylor N Bednar; Andrew D Chen; T V RajanBabu; David A Nagib
Journal:  J Am Chem Soc       Date:  2022-07-12       Impact factor: 16.383

4.  Expanding the horizon of the thymine isostere biochemistry: unique cyclobutane dimers formed by photoreaction between a thymine and a toluene residue in the dinucleotide framework.

Authors:  Degang Liu; Yan Zhou; Jingzhi Pu; Lei Li
Journal:  Chemistry       Date:  2012-05-15       Impact factor: 5.236

5.  Examining the base stacking interaction in a dinucleotide context via reversible cyclobutane dimer analogue formation under UV irradiation.

Authors:  Degang Liu; Lei Li
Journal:  RSC Adv       Date:  2013-11-14       Impact factor: 3.361

6.  Radical cascade synthesis of azoles via tandem hydrogen atom transfer.

Authors:  Andrew D Chen; James H Herbort; Ethan A Wappes; Kohki M Nakafuku; Darsheed N Mustafa; David A Nagib
Journal:  Chem Sci       Date:  2020-01-31       Impact factor: 9.825

  6 in total

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