Literature DB >> 24441417

Observations on transition metal free biaryl coupling: potassium tert-butoxide alone promotes the reaction without diamine or phenanthroline catalysts.

J Cuthbertson1, V J Gray, Jonathan D Wilden.   

Abstract

Biaryl coupling (often labelled 'C-H activation') of aromatic systems can be achieved by potassium tert-butoxide alone in the absence of any amine or bipyridine catalyst (1,10-phenanthroline or N,N'-dimethylethylenediamine being the most common), previously reported to be essential. Various mechanistic studies and observations are presented which suggest that when 1,10-phenanthroline is employed as the catalyst, the alkoxide is destroyed almost immediately.

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Year:  2014        PMID: 24441417     DOI: 10.1039/c3cc49019j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  4 in total

1.  Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.

Authors:  David E Stephens; Johant Lakey-Beitia; Jessica E Burch; Hadi D Arman; Oleg V Larionov
Journal:  Chem Commun (Camb)       Date:  2016-08-02       Impact factor: 6.222

2.  Electron transfer-induced coupling of haloarenes to styrenes and 1,1-diphenylethenes triggered by diketopiperazines and Potassium tert-butoxide.

Authors:  Eswararao Doni; Shengze Zhou; John A Murphy
Journal:  Molecules       Date:  2015-01-22       Impact factor: 4.411

3.  Small organic molecules with tailored structures: initiators in the transition-metal-free C-H arylation of unactivated arenes.

Authors:  Zhenghui Liu; Peng Wang; Yu Chen; Zhenzhong Yan; Suqing Chen; Wenjun Chen; Tiancheng Mu
Journal:  RSC Adv       Date:  2020-04-09       Impact factor: 4.036

4.  KOtBu as a Single Electron Donor? Revisiting the Halogenation of Alkanes with CBr₄ and CCl₄.

Authors:  Katie J Emery; Allan Young; J Norman Arokianathar; Tell Tuttle; John A Murphy
Journal:  Molecules       Date:  2018-05-01       Impact factor: 4.411

  4 in total

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