| Sonogashira coupling | |
|---|---|
| Named after | Kenkichi Sonogashira |
| Reaction type | Coupling reaction |
| Identifiers | |
| Organic Chemistry Portal | sonogashira-coupling |
| RSC ontology ID | RXNO:0000137 |
| Examples and Related Reactions | |
| Similar reactions | Copper-free Sonogashira coupling |
The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide.[1]
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| The Sonogashira reaction |
|---|
- R1: aryl or vinyl
- R2: arbitrary
- X: I, Br, Cl or OTf
The Sonogashira cross-coupling reaction has been employed in a wide variety of areas, due to its usefulness in the formation of carbon–carbon bonds. The reaction can be carried out under mild conditions, such as at room temperature, in aqueous media, and with a mild base, which has allowed for the use of the Sonogashira cross-coupling reaction in the synthesis of complex molecules. Its applications include pharmaceuticals, natural products, organic materials, and nanomaterials.[1] Specific examples include its use in the synthesis of tazarotene,[2] which is a treatment for psoriasis and acne, and in the preparation of SIB-1508Y, also known as Altinicline,[3] a nicotinic receptor agonist.
- ^ a b Sonogashira, K. (2002), "Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides", J. Organomet. Chem., 653 (1–2): 46–49, doi:10.1016/s0022-328x(02)01158-0
- ^ King, A.O.; Yasuda, N. (2005), "A Practical and Efficient Process for the Preparation of Tazarotene", Org. Process Res. Dev., 9 (5): 646–650, doi:10.1021/op050080x
- ^ King, A. O.; Yasuda, N. (2004), Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals Organometallics in Process Chemistry, Top. Organomet. Chem., vol. 6, pp. 205–245, doi:10.1007/b94551, ISBN 978-3-540-01603-8