Work

A Unified Approach to Couple Aromatic Heteronucleophiles to Azines and Pharmaceuticals

Year: 2018

Type: article

Abstract: 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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201807322

Authors: Ryan G. Anderson, Brianna M. Jett, Andrew McNally

Institution: Colorado State University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Foundation for the National Institutes of Health, National Institutes of Health, National Institute of General Medical Sciences

Awards: G486311021, New Chemical Process to Selectively Functionalize Pyridines, Diazines and Pharmaceuticals