Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary
| Autor: | John R. Coombs, Yang Gao, Matthew J. Goldfogel, Hou-Xiang Lu, Jiahao Chen, Xiaohan Li, Zhen Liu, Keary M. Engle |
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| Rok vydání: | 2019 |
| Předmět: |
Silylation
chemistry.chemical_element Alkenes 010402 general chemistry 01 natural sciences Borylation Catalysis Article chemistry.chemical_compound Nucleophile Heterocyclic Compounds chemistry.chemical_classification Chiral auxiliary Molecular Structure 010405 organic chemistry Alkene Aryl General Chemistry General Medicine Silanes Combinatorial chemistry 0104 chemical sciences chemistry Cyclization Electrophile Palladium |
| Zdroj: | Angew Chem Int Ed Engl |
| ISSN: | 1521-3773 |
| Popis: | We report the development of palladium(0)-catalyzed syn-selective 1,2-carboboration and -silylation reactions of alkenes containing cleavable directing groups. With B(2)pin(2) or PhMe(2)Si–Bpin as nucleophiles and aryl/alkenyl triflates as electrophiles, a broad range of mono-, di-, tri- and tetrasubstituted alkenes are compatible in these transformations. We further describe a directed dearomative 1,2-carboboration of electron-rich heteroarenes by employing this approach. Through use of a removable chiral directing group, we demonstrate the viability of achieving stereoinduction in Heck-type alkene 1,2-difunctionalization. This work introduces new avenues to access highly functionalized boronates and silanes with precise regio- and stereocontrol. |
| Databáze: | OpenAIRE |
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