Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes

A Ni catalytic system was developed for the decarboxylative coupling reaction of alkynyl carboxylic acids with organosilanes. Ni­(acac)2 and 1,10-phenanthroline showed the best result in the presence of CsF and CuF2 at 120 °C. This system tolerated the presence of alkyl, alkoxy, halogen, nitro, cyan...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 81; no. 12; pp. 5244 - 5249
Main Authors Edwin Raja, Gabriel Charles, Irudayanathan, Francis Mariaraj, Kim, Han-Sung, Kim, Jimin, Lee, Sunwoo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.06.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ARYLPROPIOLIC ACIDS
HALIDES
FUNCTIONALIZATION
NANOPARTICLES
ONE-POT SYNTHESIS
ALKYNYL CARBOXYLIC-ACIDS
ARYLATION
SONOGASHIRA REACTION
DIARYLALKYNES
ARYL CHLORIDES
Online AccessGet full text

Cover

More Information
Summary:A Ni catalytic system was developed for the decarboxylative coupling reaction of alkynyl carboxylic acids with organosilanes. Ni­(acac)2 and 1,10-phenanthroline showed the best result in the presence of CsF and CuF2 at 120 °C. This system tolerated the presence of alkyl, alkoxy, halogen, nitro, cyano, ketone, and ester functional groups. Moreover, the reaction with but-2-ynedioic acid and organosilane afforded the corresponding symmetrical diarylalkynes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00883