The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity

Organic Letters
Ashok Kumar MorriVenkata Ramana Doddi

Abstract

The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.

References

Apr 13, 2002·Organic Letters·Wang Shen, Aaron Kunzer
Dec 18, 2003·Drug Discovery Today·Hartmuth C Kolb, K Barry Sharpless
Jan 23, 2004·Chemical Society Reviews·Jaime Blanco-UrgoitiJavier Pérez-Castells
Mar 11, 2004·Chemical Reviews·Steven T Diver, Anthony J Giessert
Jun 22, 2007·Angewandte Chemie·Thiruvellore Thatai Jayanth, Chien-Hong Cheng
Jul 31, 2007·Chemical Society Reviews·Congyang Wang, Zhenfeng Xi
Aug 14, 2008·Chemical Reviews·Morten Meldal, Christian Wenzel Tornøe
Sep 20, 2008·Journal of the American Chemical Society·Alexander TrofimovVladimir Gevorgyan
Apr 16, 2010·Chemical Reviews·Ana M Lozano-VilaFrancis Verpoort
May 27, 2010·Chemical Society Reviews·Damien HabrantAri M P Koskinen
Jun 10, 2011·Chemical Society Reviews·Rafael Chinchilla, Carmen Nájera
Nov 17, 2011·Chemical Reviews·Giorgio Chelucci
Jan 12, 2012·Chemical Society Reviews·James E TaylorJonathan M J Williams
Nov 13, 2013·Organic & Biomolecular Chemistry·Rick Arneil D AranconRafael Luque

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Citations

Apr 26, 2016·The Journal of Organic Chemistry·Jessy AzizSandrine Piguel
Dec 3, 2017·Chemical Biology & Drug Design·Bing WangJianbo Sun
Nov 20, 2018·Organic & Biomolecular Chemistry·Qiang FuWei Guan
Feb 1, 2020·Organic & Biomolecular Chemistry·Maddali L N Rao, Boddu S Ramakrishna

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