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Synfacts 2025; 21(07): 703
DOI: 10.1055/a-2601-5457
Metals in Synthesis

Iridium-Catalyzed Intramolecular Alkene–Alkyne Cross-Coupling to Access Macrocyclic 1,3-Dienes

Contributor(s):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Phillip Pommerening 
Zhang X, Liu X, Li X, Wang Y, He R, Zhong G *, Zhang J *. Hangzhou Normal University and Eastern Institute of Technology, Ningbo, P. R. China
Synthesis of 12- to 26-Membered Macrocyclic Dienes by Directed Intramolecular Alkene/Alkyne Cross-Coupling.

Org. Lett. 2025;
27: 4074-4078
DOI: 10.1021/acs.orglett.5c01106
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Keywords

alkene–alkyne cross-coupling - C–H functionalization - iridium catalysis - macrocyclic 1,3-dienes

Significance

Zhong, Zhang and co-workers disclosed an iridium(I)-catalyzed intramolecular alkene–alkyne cross-coupling reaction to afford macrocyclic 1,3-dienes. This method involves an amide-directed alkenyl C–H functionalization as the key step.


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Comment

All products were obtained in good yields and excellent E/Z ratios of > 99:1.  Mechanistic control experiments, including a deuterium-labeling experiment, support the shown mechanism.


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Publication History

Article published online:
23 June 2025

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