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Nickel-catalysed Hydrodimerization of Unactivated Terminal Alkenes by Li Cheng; Jiandong Liu; Yunrong Chen; Hegui Gong is a Chemistry article available to read on EtoBox.

What is Nickel-catalysed Hydrodimerization of Unactivated Terminal Alkenes about?

Site-selective homo- and cross-hydrodimerization of terminal alkenes has remained a long-standing challenge in organic synthesis. Metal-hydride-catalysed selective dimerization, oligomerization or polymerization methods are often limited to electronically biased or small alkene substrates. Here we report the development of a nickel-catalysed protocol that enables selective homo- and cross-dimerization of unactivated linear and sterically congested terminal alkenes to afford linear alkyl‒alkyl products in good yields and high linear/branched selectivity. The process is tolerant of a range of functionalities including heteroatoms, saturated heterocycles and bioactive motifs. Mechanistic experiments reveal that the co-oxidants we used, CuBr 2 and di- tert -butyl peroxide, probably convert dialkyl‒Ni(II) intermediates to the corresponding Ni(III) species through a single-electron-transfer process. This oxidative step avoids decomposition of thermally labile dialkyl‒Ni(II) intermediates and promotes the formation of hydrodimerization products by reductive elimination of the Ni(III) complex. Without CuBr 2 , high branched selectivity was achieved, affording the methyl-branched products—w

Who reads Nickel-catalysed Hydrodimerization of Unactivated Terminal Alkenes?

Author

Li Cheng; Jiandong Liu; Yunrong Chen; Hegui Gong

Publisher

Springer Science and Business Media LLC

Published

2023

Language

EN

Field

Chemistry (Physical Sciences)