Literature DB >> 19827765

In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles.

Ilya Popov1, Hien-Quang Do, Olafs Daugulis.   

Abstract

A general method has been developed for in situ trapping of arylmetal intermediates by <span class="Chemical">halogen, <class="Chemical">span class="Chemical">sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K(3)PO(4) base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pK(a) values of 35 or less are reactive.

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Year:  2009        PMID： 19827765      PMCID： PMC2783394          DOI： 10.1021/jo9015369

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

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Authors:  W. Cameron Black; Benoit Guay; Frank Scheuermeyer
Journal:  J Org Chem       Date:  1997-02-07       Impact factor: 4.354

2.  Multiple hydrogen/lithium interconversions at the same benzene nucleus: two at the most.

Authors:  M Schlosser; L Guio; F Leroux
Journal:  J Am Chem Soc       Date:  2001-04-25       Impact factor: 15.419

3.  Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.

Authors:  J Kristensen; M Lysén; P Vedsø; M Begtrup
Journal:  Org Lett       Date:  2001-05-17       Impact factor: 6.005

4.  N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics.

Authors:  G K Surya Prakash; Thomas Mathew; Dushyanthi Hoole; Pierre M Esteves; Qi Wang; Golam Rasul; George A Olah
Journal:  J Am Chem Soc       Date:  2004-12-08       Impact factor: 15.419

5.  A new strategy for deprotonative functionalization of aromatics: transformations with excellent chemoselectivity and unique regioselectivities using t-Bu-P4 base.

Authors:  Tatsushi Imahori; Yoshinori Kondo
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

6.  A general method for copper-catalyzed arylation of arene C-H bonds.

Authors:  Hien-Quang Do; Rana M Kashif Khan; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

7.  [Ir(4)(CO)(12)]-catalyzed coupling reaction of imidazoles with aldehydes in the presence of a hydrosilane to give 2-substituted imidazoles.

Authors:  Yoshiya Fukumoto; Katsutoshi Sawada; Motoyuki Hagihara; Naoto Chatani; Shinji Murai
Journal:  Angew Chem Int Ed Engl       Date:  2002-08-02       Impact factor: 15.336

8.  Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives: a one-pot protocol to substituted azabiaryls.

Authors:  Manlio Alessi; Andrew L Larkin; Kevin A Ogilvie; Laine A Green; Sunny Lai; Simon Lopez; Victor Snieckus
Journal:  J Org Chem       Date:  2007-02-07       Impact factor: 4.354

9.  A simple base-mediated halogenation of acidic sp2 C-H bonds under noncryogenic conditions.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

10.  Bromine as the ortho-directing group in the aromatic metalation/silylation of substituted bromobenzenes.

Authors:  Sergiusz Luliński; Janusz Serwatowski
Journal:  J Org Chem       Date:  2003-11-28       Impact factor: 4.354
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  5 in total

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Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-08-08       Impact factor: 15.419

2.  Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

3.  Intercepting the Breslow intermediate via Claisen rearrangement: synthesis of complex tertiary alcohols without organometallic reagents.

Authors:  Sefat Alwarsh; Kolawole Ayinuola; Silvana S Dormi; Matthias C McIntosh
Journal:  Org Lett       Date:  2012-12-05       Impact factor: 6.005

4.  Organic Dye-Catalyzed, Visible-Light Photoredox Bromination of Arenes and Heteroarenes Using N-Bromosuccinimide.

Authors:  David A Rogers; Roxanne G Brown; Zachary C Brandeburg; Eric Y Ko; Megan D Hopkins; Gabriel LeBlanc; Angus A Lamar
Journal:  ACS Omega       Date:  2018-10-09

5.  Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines.

Authors:  Thomas R Puleo; Jeffrey S Bandar
Journal:  Chem Sci       Date:  2020-09-09       Impact factor: 9.825
  5 in total

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