33399-34-7Relevant articles and documents
A Unified Approach to Couple Aromatic Heteronucleophiles to Azines and Pharmaceuticals
Anderson, Ryan G.,Jett, Brianna M.,McNally, Andrew
supporting information, p. 12514 - 12518 (2018/09/10)
Coupling aromatic heteronucleophiles to arenes is a common way to assemble drug-like molecules. Many methods operate via nucleophiles intercepting organometallic intermediates, via Pd-, Cu-, and Ni-catalysis, that facilitate carbon-heteroatom bond formation and a variety of protocols. We present an alternative, unified strategy where phosphonium salts can replicate the behavior of organometallic intermediates. Under a narrow set of reaction conditions, a variety of aromatic heteronucleophile classes can be coupled to pyridines and diazines that are often problematic in metal-catalyzed couplings, such as where (pseudo)halide precursors are unavailable in complex structures with multiple polar functional groups.
