Literature DB >> 19102661

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

Hien-Quang Do1, Olafs Daugulis.   

Abstract

A new method has been developed for in situ halogenation of acidic sp(2) carbon-hydrogen bonds in heterocycles and electron-deficient arenes. Either selective monohalogenation or one-step exhaustive polyhalogenation is possible for substrates possessing several C-H bonds that are flanked by electron-withdrawing groups. For the most acidic arenes, such as pentafluorobenzene, K(3)PO(4) base can be employed instead of BuLi for metalation/halogenation sequences.

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Year:  2009        PMID： 19102661      PMCID： PMC2635093          DOI： 10.1021/ol802411f

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Metalation of Nitroaromatics with in Situ Electrophiles.

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.  Copper-catalyzed arylation of heterocycle C-H bonds.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2007-09-22       Impact factor: 15.419

4.  Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2008-01-09       Impact factor: 15.419

5.  A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols.

Authors:  Enrique Vazquez; Ian W Davies; Joseph F Payack
Journal:  J Org Chem       Date:  2002-10-18       Impact factor: 4.354

6.  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

7.  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

8.  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

9.  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
  9 in total
  4 in total

1.  A general method for copper-catalyzed arene cross-dimerization.

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

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

Authors:  Ilya Popov; Hien-Quang Do; Olafs Daugulis
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

3.  Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.

Authors:  Gregory J P Perry; Jacob M Quibell; Adyasha Panigrahi; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2017-08-08       Impact factor: 15.419

4.  Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer.

Authors:  Thomas R Puleo; Danielle R Klaus; Jeffrey S Bandar
Journal:  J Am Chem Soc       Date:  2021-08-04       Impact factor: 16.383
  4 in total

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