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Electrochemical Deoxygenative Silylation of Alcohols
Piret Villo1, Malin Lill1, Ziwei Fan1
1Department of Chemistry, KTH Royal Institute of Technology, Stockholm, SE-10044, Sweden.
Abstract:
Alcohols are highly common organic compounds but remain scarce as alkyl donors in synthetic procedures. Here, we describe an electrochemical procedure for their deoxygenative cross-electrophile coupling with hydrosilanes, furnishing organosilane products in good to excellent yields. Mechanistic studies provide insights into the operating pathways of this semi-paired electrolytic transformation, suggesting that silyl ethers are likely reaction intermediates. Furthermore, a unified mechanistic proposal is presented that accounts for observed reactivity differences with analogous deoxygenative electrocarboxylation.
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