page_title: Sonogashira coupling
section_title: Pharmaceuticals
hierarchical_section_title: Sonogashira coupling / Applications in Synthesis / Natural products / Pharmaceuticals
caption_attribution_description: English: Reaction scheme redrawn from Bakherad-Tetrahedron-Lett-2008
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 versatility of the Sonogashira reaction makes it a widely used reaction in the synthesis of a variety of compounds. One such pharmaceutical application is in the synthesis of SIB-1508Y, which is more commonly known as Altinicline. Altinicline is a nicotinic acetylcholine receptor agonist that has shown potential in the treatment of Parkinson’s disease, Alzheimer’s disease, Tourette’s syndrome, Schizophrenia, and attention deficit hyperactivity disorder (ADHD). As of 2008, Altinicline has undergone Phase II clinical trials.
  Illustrating the Sonogashira cross coupling reactions is in the synthesis of imidazopyridine derivatives.
caption: synthesis of imidazopyridine derivatives.[51]
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