Ligand-enabled Ni-catalysed dicarbofunctionalisation of alkenes with diverse native functional groups

Dao-Ming Wang, Hui-Mei Shan, Li-Qin She, Yu-Qing He, Yichen Wu, Yong Tang, Li-Ping Xu () and Peng Wang ()
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Dao-Ming Wang: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
Hui-Mei Shan: Shandong University
Li-Qin She: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
Yu-Qing He: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
Yichen Wu: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
Yong Tang: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
Li-Ping Xu: Shandong University
Peng Wang: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract The transition metal-catalysed dicarbofunctionalisation of unactivated alkenes normally requires exogenous strong coordinated directing groups, thus reducing the overall reaction efficiency. Here, we report a ligand-enabled Ni(II)-catalysed dicarbofunctionalisation of unactivated alkenes with aryl/alkenyl boronic acids and alkyl halides as the coupling partners with a diverse range of native functional groups as the directing group. This dicarbofunctionalisation protocol provides an efficient and direct route towards vicinal 1,2-disubstituted alkanes using primary, secondary, tertiary amides, sulfonamides, as well as secondary and tertiary amines 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, supporting by both experimental and computational studies. This dicarbofunctionalisation reaction features the use of native directing group, a broad substrate scope, and excellent scalability.

Date: 2024
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DOI: 10.1038/s41467-024-54170-9

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