Mandigma, Mark John P. and Domanski, Michal and Barham, Joshua P. (2020) C-Alkylation of alkali metal carbanions with olefins. ORGANIC & BIOMOLECULAR CHEMISTRY, 18 (39). pp. 7697-7723. ISSN 1477-0520, 1477-0539
Full text not available from this repository. (Request a copy)Abstract
C-Alkylations of alkali metal carbanions with olefins, first reported five decades ago, is a class of reaction undergoing a resurgence in organic synthesis in recent years. As opposed to expectations from classical chemistry and transition metal-catalysis, here olefins behave as closed-shell electrophiles. Reactions range from highly reactive alkyllithiums giving rise to anionic polymerization, to moderately reactive alkyl-potassium or alkylsodium compounds that give rise to defined, controlled and bimolecular chemistry. This review presents a brief historical overview on C-alkylation of alkali metal carbanions with olefins (typically mediated by KOtBu and KHMDS), highlights contemporary applications and features developing mechanistic understanding, thereby serving as a platform for future studies and the widespread use of this class of reaction in organic synthesis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | BASE-CATALYZED REACTIONS; SIDE-CHAIN ALKENYLATION; POTASSIUM TERT-BUTOXIDE; H BOND ADDITION; ANIONIC-POLYMERIZATION; ALPHA-METHYLSTYRENE; ENANTIOSELECTIVE CARBOLITHIATION; ISOPRENE POLYMERIZATION; EQUILIBRIUM ACIDITIES; AROMATIC-HYDROCARBONS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Petra Gürster |
| Date Deposited: | 20 Apr 2021 11:23 |
| Last Modified: | 20 Apr 2021 11:23 |
| URI: | https://pred.uni-regensburg.de/id/eprint/43536 |
Actions (login required)
 |
View Item |
