page_title: Sonogashira coupling
section_title: Enynes and enediynes
hierarchical_section_title: Sonogashira coupling / Applications in Synthesis / Natural products / Enynes and enediynes
caption_attribution_description: English: Reaction scheme from Shao-J-Org-Chem-2005
context_page_description: 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.
  R¹: aryl
  R²: aryl or vinyl
  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. Specific examples include its use in the synthesis of tazarotene, which is a treatment for psoriasis and acne, and in the preparation of SIB-1508Y, also known as Altinicline, a nicotinic receptor agonist.
context_section_description: The 1,3-enyne moiety is an important structural unit for biologically active and natural compounds. It can be derived from vinylic systems and terminal acetylenes by using a configuration-retention stereospecific procedure such as the Sonogashira reaction. Vinyl iodides are the most reactive vinyl halides to Pd⁰ oxidative addition, and their use is therefore most frequent for Sonogashira cross-coupling reactions due to the usually milder conditions employed. Some examples include:
  Thongsornkleeb C.; Danhaiser R. L (2005). "The coupling of 2-iodo-prop-2-enol with a wide range of acetylenes such as TMSA to give enynyl alcohol, which can be oxidized to the corresponding R-alkynylated acroleins". Journal of Organic Chemistry. 70: 2364. doi:10.1021/jo047869a. PMC 2897060. PMID 15760233.
  The preparation of an alk-2-ynylbuta-1,3-dienes from the cross-coupling of a diiodide and phenylacetylene, as shown below.
caption: Synthesis of an alk-2-ynylbuta-1,3,-diene accomplished by Sonogashira coupling.[47]
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