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

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α-Tertiary Dialkyl Ether Synthesis via Reductive Photocatalytic α-Functionalization of Alkyl Enol Ethers
ACS Catalysis ( IF 11.3 ) Pub Date : 2020-09-08 , DOI: 10.1021/acscatal.0c02584
Jamie A. Leitch ₁ , Thomas Rossolini ₁ , Tatiana Rogova ₁ , Darren J. Dixon ₁

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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.

中文翻译：

烷基烯醇醚的还原光催化α-官能化合成α-叔二烷基醚

描述了在蓝色LED辐射下，在Hantzsch酯末端还原剂的存在下，通过使用共轭烯烃对烯醇醚底物进行还原性α-官能化，对富C（sp ³）的α-叔二烷基醚进行的光催化结构。通过最初的TMSC1促进烯醇醚底物的质子活化来生成氧碳鎓离子，随后单电子转移至该中间体，将推定的亲核性α-氧基叔叔自由基与多种烯烃底物有效地结合。还原性官能化策略相对于烯烃受体和烯醇醚供体片段均易于执行，有效且范围广泛，并提供了多种复杂的α-叔二烷基醚结构。

更新日期：2020-10-02

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