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Updated: May 27, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Nickel-Catalyzed Linear-Selective C-H Alkylation of N-Heteroarenes with Unactivated α-Olefins
Yang Liu1, Wen-Hui Jin1, Rui-Peng Li1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Abstract:
We herein describe the nickel-catalyzed C2-H alkylation of benzothiazoles with unactivated α-olefins by using the Ni(IPr*OMe)[P(OEt)3]Br2/Mg catalytic system in which a variety of linear alkylated benzothiazoles with high regioselectivity were formed under mild reaction conditions. This transformation showed good compatibility to unactivated α-olefins bearing various functional groups, such as esters, acetals, silyl ethers, amines, silanes, and boronate esters. Furthermore, this transformation is also suitable to other typical N-heteroarenes including thiazoles, benzimidazoles, quinazolones, uracils, pyridines, caffeines, and indoles. Thus, this work provides rapid access to diverse linear alkylated N-heteroarenes with good step and atom economy.
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