Scope and Mechanistic Aspect of Nickel-Catalyzed Alkenylation of Benzothiazoles and Related Azoles with Styryl Bromides
| Autor: | Benudhar Punji, Ulhas N. Patel, Rahul A. Jagtap |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Oxidative addition Combinatorial chemistry Reductive elimination 0104 chemical sciences Catalysis Inorganic Chemistry chemistry.chemical_compound Nickel Benzothiazole chemistry Bromide Reactivity (chemistry) Physical and Theoretical Chemistry Bond cleavage |
| Zdroj: | Organometallics. 38:2422-2430 |
| ISSN: | 1520-6041 0276-7333 |
| DOI: | 10.1021/acs.organomet.9b00060 |
| Popis: | Alkenylation of benzothiazoles and related azoles with alkenyl bromides is achieved employing the well-defined and air-stable nickel complexes, (bpy)NiBr2 and [Ni(bpy)3][NiBr4], as catalysts. Numerous electronically distinct alkenyl bromides efficiently coupled with substituted benzothiazoles, oxazoles, and benzimidazoles under the catalytic conditions to afford 2-alkenylated azoles. An extensive mechanistic study of the alkenylation of benzothiazole using (bpy)NiBr2 highlights a single-electron transfer process for the reaction involving the two-step one-electron oxidative addition of alkenyl bromide. The substrate benzothiazole plays a significant and diverse role in the reaction, and C–H bond cleavage is reversible in nature. Detailed kinetic analysis and control reactivity studies are indicative of a Ni(I)/Ni(III) pathway for the alkenylation comprising the rate-influencing reductive elimination step. |
| Databáze: | OpenAIRE |
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