Chan–Lam Amination of Secondary and Tertiary Benzylic Boronic Esters
| Autor: | Francesca M. Dennis, James D Grayson, Craig C. Robertson, Benjamin M. Partridge |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
inorganic chemicals
Reaction mechanism Allylic rearrangement Primary (chemistry) 010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Coupling reaction 0104 chemical sciences Transmetalation chemistry.chemical_compound Aniline chemistry Reagent Amination |
| Zdroj: | The Journal of Organic Chemistry. 86:9883-9897 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c00976 |
| Popis: | We report a Chan-Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines to form valuable alkyl amine products. Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition-metal-mediated transformation of a tertiary alkylboron reagent. Initial investigation into the reaction mechanism suggests that transmetalation from B to Cu occurs through a single-electron, rather than a two-electron process. |
| Databáze: | OpenAIRE |
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