External-Ligand-Free, Nickel-Catalyzed Alkenylation of N-Sulfonylamines with Internal Alkynes

Jia-Yue Li; Lun Li; Yun-Zhi Lin; Hang Shi

doi:10.1055/s-0040-1719913

Synthesis, Table of Contents

Synthesis 2022; 54(15): 3341-3350
DOI: 10.1055/s-0040-1719913

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External-Ligand-Free, Nickel-Catalyzed Alkenylation of N-Sulfonylamines with Internal Alkynes

Authors

Jia-Yue Li‡

^aZhejiang University, Hangzhou 310027, Zhejiang Province, P. R. of China

^bKey Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China
Lun Li‡

^bKey Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China
Yun-Zhi Lin

^bKey Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China
Hang Shi ∗

^bKey Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China

^cInstitute of Natural Sciences, Westlake Institute for Advanced Study, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, P. R. of China

Abstract

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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.

Key words

nickel - ligand-free - N-sulfonylallylic amine - alkenylation - cyclometallation

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References

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Supplementary Material

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