Deoxygenative C鈥揅 Bond-Forming Processes via a Net Four-Electron Reductive Coupling

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• 作者：David P. Todd ; Benjamin B. Thompson ; Alex J. Nett ; John Montgomery
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：October 14, 2015
• 年：2015
• 卷：137
• 期：40
• 页码：12788-12791
• 全文大小：325K
• ISSN：1520-5126

文摘

The nickel-catalyzed coupling of enones or enals with alkynes in the presence of silane and titanium alkoxide reductants provides direct access to skipped diene products. The process involves a net four-electron reductive coupling and proceeds with deoxygenation of the starting enone or enal. A new class of well-defined nickel(0) precatalysts bearing an unhindered N-heterocyclic carbene ligand, which was developed in optimization of the process, is essential for the efficiency of the transformation. The strategy allows the high reactivity of 伪,尾-unsaturated carbonyl substrates to be utilized in couplings with simultaneous extrusion of the oxygen atom, thus enabling a traceless strategy for alkene installation.