Alkene Dicarbofunctionalisation via High-Valent Nickel Catalysis

16 April 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Great advances have been made by leveraging high-valent Pd(II)/Pd(IV) catalysis in the areas of C–H activation and alkene difunctionalisation, thus representing a powerful approach for the construction of carbon-carbon and carbon-heteroatom bond. However, the catalytic reactions involving high-valent Ni(II)/Ni(IV) catalysis are largely underdeveloped. Here we report a Ni(II)-catalysed dicarbofunctionalisation of unactivated alkenes via high-valent Ni(II)/Ni(IV) catalysis. This dicarbofunctionalisation protocol provides a highly efficient and direct route towards vicinal substituted alkanes using primary, secondary, and tertiary amides, as well as secondary and tertiary amines as the native directing group under redox-neutral conditions that are challenging to access through conventional methods. The key to the success of this reaction is the use of a bulky β-diketone ligand, which could enable the insertion of alkene to aryl-Ni(II) species, stabilize the alkyl-Ni(II) species and inhibit the homolytic alkyl-Ni(II) cleavage. This dicarbofunctionalisation reaction features the use of native directing group, a broad substrate scope, and excellent scalability. The resulting Weinreb amide-derived products can be readily derivatized to a variety of ketones and aldehyde, which are fundamentally useful in synthetic chemistry. In addition, this protocol has been employed for the efficient preparation of several bioactive compounds, showcasing the significant synthetic values of our current method.


β-diketone ligand
Alkene Dicarbofunctionalisation
Unactivated Alkene
Native Directing Group

Supplementary materials

Supplementary Information-NiDicarbofunctionalisation
Supplementary Information


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.