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Synthesis 2022; 54(15): 3341-3350
DOI: 10.1055/s-0040-1719913
DOI: 10.1055/s-0040-1719913
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External-Ligand-Free, Nickel-Catalyzed Alkenylation of N-Sulfonylamines with Internal Alkynes
This work was supported by the ‘Pioneer’ and ‘Leading Goose’ R & D Program of Zhejiang (2022SDXHDX0006) and the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang (2020R01004).
Abstract
Allylic amines were synthesized via a nickel-catalyzed coupling reaction between various N-sulfonylamines and internal alkynes. The catalytic reaction was by-product-free and proceeded without the need for additional oxidant/reductant or activating reagent. As improvements over established methods, the present approach avoids the need for an external ligand, which increases the value of the approach with respect to atom economy, and it uses bench-stable Ni(II)Br2(dme) instead of Ni(0)(COD)2 as the source of the nickel catalyst. Mechanistic studies revealed that a catalytic amount of a strong base (i.e., KO t Bu) was essential for the formation of active Ni(0) catalyst, which, along with an imine intermediate, then initiated the catalytic cycle.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719913.
- Supporting Information
Publication History
Received: 18 January 2022
Accepted after revision: 18 February 2022
Article published online:
20 April 2022
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For selected examples of nickel-catalyzed α-alkylation reactions with olefin, see: