Download PDF
Synfacts 2025; 21(01): 56
DOI: 10.1055/a-2467-6312
Metals in Synthesis

Copper-Accelerated Palladium-Catalyzed Cross-Coupling of Terminal Alkynes and sp2 C–X Bonds

Contributor(s):
Mark Lautens 
,
Andrew G. Durant
Sonogashira K, Tohda Y, Hagihara N. Osaka University, Japan
A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines.

Tetrahedron Lett. 1975;
16: 4467-4470
CrossrefPubMedSearch in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Keywords

palladium - copper - alkynes - cross-coupling

Significance

Three decades ago Sonogashira et al. reported the cross-coupling of terminal alkynes with sp2 C–X bonds. They reported the coupling of various vinylic bromides and (hetero)aryl iodides and bromides with acetylene, phenylacetylene, and propargyl alcohol.


#

Comment

The authors build upon previous work coupling copper acetylides with iodoarenes and iodoalkenes. They were able to generate a copper acetylide in situ from a terminal alkyne, copper iodide, and diethylamine. The reaction is very efficient for the synthesis of internal alkynes.


#
#

Publication History

Article published online:
20 December 2024

© 2024. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany


   Permissions and Reprints