Williams, Matthew TJ;
Morrill, Louis C;
Browne, Duncan L;
(2023)
Nickel-Catalyzed Intramolecular Alkene Difunctionalization by Ball-Milling.
Advanced Synthesis and Catalysis
10.1002/adsc.202300188.
(In press).
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Abstract
A mechanochemical nickel-catalyzed intramolecular difunctionalization reaction of alkene tethered aryl halides with alkyl halides is herein described. This method allows for synthesis of 3,3-disubstituted heterocycles, namely oxindoles, with shorter reaction times than solution-phase counterparts. Additionally, this process is solvent minimized, with DMA used in liquid-assisted grinding (LAG) quantities and circumvents the need for chemical activation of the terminal reductant (manganese) through mechanical grinding. The process can be scaled up to yield over a gram of product and modest enantioinduction is possible by utilizing a chiral PyrOx ligand. (Figure presented.).
| Type: | Article |
|---|---|
| Title: | Nickel-Catalyzed Intramolecular Alkene Difunctionalization by Ball-Milling |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/adsc.202300188 |
| Publisher version: | https://doi.org/10.1002/adsc.202300188 |
| Language: | English |
| Additional information: | © 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| Keywords: | Mechanochemistry, Ball-mill, Nickel-catalysis, Solvent-minimized, Heterocycles |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10169582 |
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