Literature DB >> 11529781

Synthesis of diynes and tetraynes from in situ desilylation/dimerization of acetylenes.

M A Heuft1, S K Collins, G P Yap, A G Fallis.   

Abstract

[reaction: see text]. An efficient method for the in situ desilylation/oxidative dimerization of (trialkylsilyl)acetylenes is described. This protocol avoids the complications encountered with sensitive diynes by eliminating the deprotection and isolation steps. Various aromatic and alkyl diynes and tetraynes can be synthesized in a straightforward manner in good yields (82-99%) from TIPS-protected acetylenes. This method facilitates the efficient synthesis of novel tetrayne-bridged acetylenic cyclophanes 6 and 7 in a direct manner.

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Year:  2001        PMID: 11529781     DOI: 10.1021/ol016414u

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


  6 in total

1.  A Short Synthesis of (S)-(+)-Siphonodiol.

Authors:  Benjamin W Gung; Derek T Craft; Jessica Truelove
Journal:  Tetrahedron Asymmetry       Date:  2007-06-22

2.  A facile copper(I)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Org Biomol Chem       Date:  2013-11-21       Impact factor: 3.876

3.  A Concise Synthesis of R-(-)-Cicutoxin, a Natural 17-Carbon Polyenyne.

Authors:  Benjamin W Gung; Ann O Omollo
Journal:  European J Org Chem       Date:  2009-03-01

4.  Synthesis of alpha-tetrasubstituted triazoles by copper-catalyzed silyl deprotection/azide cycloaddition.

Authors:  Zachary L Palchak; Paula T Nguyen; Catharine H Larsen
Journal:  Beilstein J Org Chem       Date:  2015-08-14       Impact factor: 2.883

5.  Quantitative Structure-Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl-Substituted Derivatives.

Authors:  Gaël Rouillé; Cornelia Jäger; Friedrich Huisken; Thomas Henning; Regina Czerwonka; Gabriele Theumer; Carsten Börger; Ingmar Bauer; Hans-Joachim Knölker
Journal:  ChemistryOpen       Date:  2017-07-13       Impact factor: 2.911

6.  Novel Anticancer NHC*-Gold(I) Complexes Inspired by Lepidiline A.

Authors:  Danielle Curran; Helge Müller-Bunz; Sofia I Bär; Rainer Schobert; Xiangming Zhu; Matthias Tacke
Journal:  Molecules       Date:  2020-07-30       Impact factor: 4.411

  6 in total

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