Copper-Catalyzed Cross-Nucleophile Coupling of β‑Allenyl Silanes with Tertiary C–H Bonds: A Radical Approach to Branched 1,3-Dienes
journal contributionposted on 19.07.2021, 19:33 by Qi-Chao Shan, Lu-Min Hu, Wei Qin, Xu-Hong Hu
Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)–H dienylation proceeded in a regiospecific manner, even in the presence of competitive C–H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.
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Describedcopper catalysisAllenylsitedieneoxygen atomnucleophilic substratesCopper-Catalyzed Cross-Nucleophileregiospecific mannerpresenceintermediacySilanefunctionalityapproachcontrol experiments supportfunctionalized alkyl radicalsdienylationBranchedoxidativeBondbenzylicRadical Approachhydrogen atom transfer processDienehydrocarbons appendingβ- allenyl silanesTertiarybond