Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates
| Autor: | Alexandre A Mikhailine, Gabriela A Grasa Mannino, Thomas J. Colacot |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Organic Chemistry Imine 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Aniline chemistry Nucleophile Electrophile Benzophenone Amine gas treating Physical and Theoretical Chemistry Amination BINAP |
| Zdroj: | Organic Letters. 20:2301-2305 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.8b00646 |
| Popis: | A chemoselective sequential one-pot coupling protocol was developed for preparing several amino-anilines in high yield as building blocks for active pharmaceutical ingredients (APIs). Site (Cl vs Br on electrophile) and nucleophile (amine vs imine) selectivity is dictated by the catalyst employed. A Pd-crotyl (t-BuXPhos) precatalyst selectively coupled the Ar-Br of the polyhaloarene with benzophenone imine, even in the presence of a secondary amine, while Pd-based RuPhos or (BINAP)Pd(allyl)Cl coupled the Ar-Cl site with secondary amines. |
| Databáze: | OpenAIRE |
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