Leitch, JA;
Rossolini, T;
Rogova, T;
Dixon, DJ;
(2020)
α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers.
ACS Catalysis
, 10
(19)
pp. 11430-11437.
10.1021/acscatal.0c02584.
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Abstract
The photocatalytic construction of C(sp3)-rich α-tertiary dialkyl ethers through the reductive α-functionalization of alkyl enol ether substrates with conjugated alkenes in the presence of a Hantzsch ester terminal reductant under blue LED irradiation is described. Pivoting on oxocarbenium ion generation via an initial TMSCl-facilitated protic activation of the enol ether substrate, subsequent single-electron transfer to this intermediate delivers the putative nucleophilic α-oxy tertiary radical capable of productively combining with a variety of alkene substrates. The reductive functionalization strategy was simple to perform, efficient, broad in scope with respect to both alkene acceptor and enol ether donor fragments, and delivered a wide range of complex α-tertiary dialkyl ether architectures.
| Type: | Article |
|---|---|
| Title: | α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1021/acscatal.0c02584 |
| Publisher version: | https://doi.org/10.1021/acscatal.0c02584 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| Keywords: | ether photoredox catalysis reductive radicals quaternary center |
| 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-pp.ucl.ac.uk/id/eprint/10122634 |
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