Literature DB >> 12227823

Bulky trialkylsilyl acetylenes in the Cadiot-Chodkiewicz cross-coupling reaction.

Joseph P Marino1, Hanh Nho Nguyen.   

Abstract

Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and triisopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio- and stereoselectively into enynes by hydrotelluration, carbometalation, and reduction reactions.

Entities:  

Year:  2002        PMID： 12227823     DOI： 10.1021/jo025745x

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


  13 in total

1.  Mechanism of the Intramolecular Hexadehydro-Diels-Alder Reaction.

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Journal:  J Org Chem       Date:  2015-08-25       Impact factor: 4.354

2.  Application of the Solid-Supported Glaser-Hay Reaction to Natural Product Synthesis.

Authors:  Jessica S Lampkowski; Diya M Uthappa; John F Halonski; Johnathan C Maza; Douglas D Young
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3.  Expanding the scope of alkyne-mediated bioconjugations utilizing unnatural amino acids.

Authors:  Johnathan C Maza; Zachary M Nimmo; Douglas D Young
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

4.  Selectivity in the ruthenium-catalyzed alder ene reactions of di- and triynes.

Authors:  Eun Jin Cho; Daesung Lee
Journal:  J Am Chem Soc       Date:  2007-05-08       Impact factor: 15.419

5.  Structure and reactivity of alkynyl ruthenium alkylidenes.

Authors:  Sang Young Yun; Mansuk Kim; Daesung Lee; Donald J Wink
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

6.  Total synthesis of (3R,9R,10R)-panaxytriol via tandem metathesis and metallotropic [1,3]-shift as a key step.

Authors:  Eun Jin Cho; Daesung Lee
Journal:  Org Lett       Date:  2007-12-13       Impact factor: 6.005

7.  Synthesis of D-abrines by palladium-catalyzed reaction of ortho-iodoanilines with N-Boc-N-methylalanyl-substituted acetaldehyde and acetylene.

Authors:  Paulami Danner; Marius Morkunas; Martin E Maier
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005

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

Authors:  Phil C Knutson; Haleigh E Fredericks; Eric M Ferreira
Journal:  Org Lett       Date:  2018-10-17       Impact factor: 6.005

9.  Benzotriazole as an Efficient Ligand in Cu-Catalyzed Glaser Reaction.

Authors:  Mala Singh; Anoop S Singh; Nidhi Mishra; Anand K Agrahari; Vinod K Tiwari
Journal:  ACS Omega       Date:  2019-01-31

10.  Synthesis of isochromene-type scaffolds via single-flask Diels-Alder-[4 + 2]-annulation sequence of a silyl-substituted diene with menadione.

Authors:  Jihoon Lee; James S Panek
Journal:  Org Lett       Date:  2014-06-11       Impact factor: 6.005
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