33399-34-7Relevant academic research and scientific papers
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.
Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
Moser, Daniel,Duan, Yaya,Wang, Feng,Ma, Yuanhong,O'Neill, Matthew J.,Cornella, Josep
, p. 11035 - 11039 (2018/07/31)
The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C?N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C?O, C?N, C?S, or C?SO2R bonds are disclosed herein. In contrast to C?N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional-group tolerance. In addition to small-molecule derivatization, Pyry-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.
