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. 2022 Dec 27;8(1):1060-1066.
doi: 10.1021/acsomega.2c06417. eCollection 2023 Jan 10.

Ni-Catalyzed Regioselective Reductive 1,3-Dialkenylation of Alkenes

Laura M Wickham  1 , Roshan K Dhungana  1 , Ramesh Giri  1
Affiliations

Ni-Catalyzed Regioselective Reductive 1,3-Dialkenylation of Alkenes

Laura M Wickham et al. ACS Omega. .

Abstract

Dicarbofunctionalization is an important efficient synthetic technique for adding two chemical moieties across an alkene. Here, a novel method of reductive dicarbofunctionalization has been developed using a single alkenyl triflate as the electrophile, combined with an unactivated alkene. The reaction does not require an external auxiliary and proceeds with complete regioselectivity.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Strategies for Dicarbofuctionalization
Scheme 2
Scheme 2. Selected Examples of Reductive Dicarbofunctionalization and This Work
Scheme 3
Scheme 3. Hydrolysis and Confirmation of Regioselectivity of Dialkeynylation Reaction
Scheme 4
Scheme 4. Scope with Alkenes and Alkenyl Triflates
Isolated from 0.5 mmol. Phenpropylzinc bromide (1.5 equiv) and vinyl triflate (2 equiv) were used. dr was determined by 1H NMR of the crude reaction mixture. The value in parentheses is 1H NMR yield using pyrene as an internal standard. Isolated from 1.0 mmol. dr was determined by 1H NMR of the isolated product.
Figure 1
Figure 1
Sensitivity assessment of the dialkenylation reaction illustrated as a color-coded radar diagram.
See this image and copyright information in PMC

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