α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers

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α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers

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. Green open access

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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.ucl.ac.uk/id/eprint/10122634