Literature DB >> 30336061

Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes.

Phil C Knutson1, Haleigh E Fredericks1, Eric M Ferreira1.   

Abstract

A convenient Cadiot-Chodkiewicz protocol that facilitates the use of low molecular weight alkyne coupling partners is described. The method entails an in situ elimination from a dibromoolefin precursor and immediate subjection to copper-catalyzed conditions, circumventing the hazards of volatile brominated alkynes. The scope of this method is described, and the internal 1,3-diyne products are preliminarily evaluated in ruthenium-catalyzed azide-alkyne cycloadditions.

Entities:  

Year:  2018        PMID： 30336061      PMCID： PMC6217962          DOI： 10.1021/acs.orglett.8b02975

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


  55 in total

Review 1.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

2.  Concise Total Synthesis of Ivorenolide B.

Authors:  Felix Ungeheuer; Alois Fürstner
Journal:  Chemistry       Date:  2015-07-03       Impact factor: 5.236

3.  1,1-Dibromo-1-alkenes as valuable partners in the copper-catalyzed direct alkynylation of azoles.

Authors:  Beatriz Pacheco Berciano; Sabrina Lebrequier; François Besselièvre; Sandrine Piguel
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

4.  Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy.

Authors:  Eric T Newcomb; Phil C Knutson; Blaine A Pedersen; Eric M Ferreira
Journal:  J Am Chem Soc       Date:  2015-12-30       Impact factor: 15.419

5.  Synthesis of 1,3-diynes via palladium-catalyzed reaction of 1, 1-dibromo-1-alkenes.

Authors:  W Shen; S A Thomas
Journal:  Org Lett       Date:  2000-09-07       Impact factor: 6.005

6.  Unprecedented Cu-catalyzed coupling of internal 1,3-diynes with azides: one-pot tandem cyclizations involving 1,3-dipolar cycloaddition and carbocyclization furnishing naphthotriazoles.

Authors:  Anil K Mandadapu; Sudhir K Sharma; Sahaj Gupta; Deevi G Venkata Krishna; Bijoy Kundu
Journal:  Org Lett       Date:  2011-05-17       Impact factor: 6.005

7.  Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism.

Authors:  Brant C Boren; Sridhar Narayan; Lars K Rasmussen; Li Zhang; Haitao Zhao; Zhenyang Lin; Guochen Jia; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-06-21       Impact factor: 15.419

8.  Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications.

Authors:  Johan R Johansson; Tamás Beke-Somfai; Anna Said Stålsmeden; Nina Kann
Journal:  Chem Rev       Date:  2016-11-18       Impact factor: 60.622

9.  Total Synthesis and Stereochemical Revision of 4,8-Dihydroxy-3,4-dihydrovernoniyne.

Authors:  Suresh Kanikarapu; Kanakaraju Marumudi; Ajit C Kunwar; Jhillu S Yadav; Debendra K Mohapatra
Journal:  Org Lett       Date:  2017-08-01       Impact factor: 6.005

10.  CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: an efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a]quinazolines.

Authors:  Selvarangam E Kiruthika; Paramasivan Thirumalai Perumal
Journal:  Org Lett       Date:  2013-12-30       Impact factor: 6.005
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  1 in total

Review 1.  Cross-coupling reactions towards the synthesis of natural products.

Authors:  Shaheera Tabassum; Ameer Fawad Zahoor; Sajjad Ahmad; Razia Noreen; Samreen Gul Khan; Hamad Ahmad
Journal:  Mol Divers       Date:  2021-02-20       Impact factor: 2.943
  1 in total

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