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Synfacts 2024; 20(02): 0170
DOI: 10.1055/s-0043-1772965
Metals in Synthesis

The Murahashi Reaction: Palladium-Catalyzed Cross-Coupling of Vinyl Halides with Organolithium Reagents

Rezensent(en):
Martin Oestreich
,
Hendrik F. T. Klare
,
Nektarios Kranidiotis-Hisatomi
Murahashi S.-i, *, Yamamura M, Yanagisawa K, Mita N, Kondo K. Osaka University, Japan
Stereoselective Synthesis of Alkenes and Alkenyl Sulfides from Alkenyl Halides Using Palladium and Ruthenium Catalysts.

J. Org. Chem. 1979;
44: 2408-2417
DOI: 10.1021/jo01328a016
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Key words

alkenes - cross-coupling - organolithium reagents - palladium catalysis - vinyl halides

Significance

While Murahashi initially reported his reaction in 1975 (J. Organomet. Chem. 1975, 91, C39), the catalytic variant of the Murahashi coupling was disclosed in 1979 by the same research group. The stereoselective C(sp2)–C(sp3) cross-coupling reaction of vinyl halides with organolithium reagents offers access to a range of alkenes in moderate to good yields. Since its discovery, the Murahashi reaction remained overlooked for over 30 years primarily due to the high reactivity and low functional-group tolerance of the organolithium coupling partner.


 

Comment

Building on Feringa‘s pioneering contribution (Nat. Chem. 2013, 5, 667), several research groups have been actively involved in enhancing this reaction, eventually leading to its revival. Presently, the utilization of earth-abundant metal catalysts and the application of flow reactors are viable options.


 

Review

S. Hazra, C. C. C. Johansson Seechurn, S. Handa, T. J. Colacot ACS Catal. 2021 , 11, 13188–13202.


 

 

Publikationsverlauf

Artikel online veröffentlicht:
16. Januar 2024

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