Corey-Fuchs Reaction

The Corey-Fuchs reaction, also known as the Ramirez-Corey-Fuchs reaction, is based on a special case of the Wittig Reaction, where the phosphorus ylide is formed from dibromocarbene. This carbene is generated in situ from the reaction of Triphenylphosphine and carbon tetrabromide.

Triphenylphosphine then attacks the nascent carbene to form the reactive ylide. This ylide undergoes a Wittig Reaction when exposed to an aldehyde.

The dibromoalkene reacts with butyllithium via deprotonation. Next, the resulting species ejects bromide through an beta-elimination pathway to produce the alkyne.

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References :

[1]Gilbert A M, Miller R, Wulff W D. Synthetic studies towards the total synthesis of olivin: Synthesis of a fully functionalized alkyne appropriate for the benzannulation reaction[J]. Tetrahedron, 1999, 55(6): 1607-1630.

[2]Zeng X, Zeng F, Negishi E. Efficient and selective synthesis of 6, 7-dehydrostipiamide via Zr-catalyzed asymmetric carboalumination and Pd-catalyzed cross-coupling of organozincs[J]. Organic Letters, 2004, 6(19): 3245-3248.

[3]Sahu B, Muruganantham R, Namboothiri I N N. Synthetic and Mechanistic Investigations on the Rearrangement of 2, 3‐Unsaturated 1, 4‐Bis (alkylidene) carbenes to Enediynes[J]. 2007.

[4]Wang Z, Campagna S, Yang K, et al. A practical preparation of terminal alkynes from aldehydes[J]. Journal of Organic Chemistry, 2000, 65(6): 1889-1891.

[5]Gibtner T, Hampel F, Gisselbrecht J P, et al. End‐cap stabilized oligoynes: model compounds for the linear sp carbon allotrope carbyne[J]. Chemistry–A European Journal, 2002, 8(2): 408-432.

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