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

submitted on 12.06.2020, 11:16 and posted on 15.06.2020, 08:56 by Jamie Leitch, Thomas Rossolini, Tatiana Rogova, Darren J. Dixon
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 delivers the key nucleophilic α-oxy tertiary radical capable of productively combining with a variety of alkene substrates. The new 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.


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University of Oxford


United Kingdom

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