Copper‐Catalyzed Borocarbonylative Coupling of Internal Alkynes with Unactivated Alkyl Halides: Modular Synthesis of Tetrasubstituted β‐Borylenones
| Autor: | Li-Jie Cheng, Neal P. Mankad |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Ketone Chemistry 010405 organic chemistry Halogenation Halide chemistry.chemical_element General Chemistry General Medicine 010402 general chemistry Copper Combinatorial chemistry 01 natural sciences Catalysis Coupling reaction 0104 chemical sciences Coupling (electronics) chemistry.chemical_compound Enone Alkyl |
| Zdroj: | Angewandte Chemie. 130:10485-10489 |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.201804883 |
| Popis: | Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β-position, using a copper-catalyzed four-component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2 pin2 ), and CO. A broad scope of highly functionalized β-borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all-carbon tetrasubstituted enones was realized by employing the β-borylated enone unit, without purification, in a Suzuki-Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products. |
| Databáze: | OpenAIRE |
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