Copper-catalyzed conjugate addition of allene-derived nucleophiles to alkenyl-substituted carboxamides

Bin Fu ¹Yue Zhao ²Xiuping Yuan ²Yanfei Li ²Jianjun Yin ²Simin Wang ²Tao Xiong ²Qian Zhang³

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作者信息

1. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis,Department of Chemistry,Northeast Normal University,Changchun 130024,China;School of Chemistry and Environmental Engineering,Changchun University of Science and Technology,Changchun 130012,China
2. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis,Department of Chemistry,Northeast Normal University,Changchun 130024,China
3. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis,Department of Chemistry,Northeast Normal University,Changchun 130024,China;State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China
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Abstract

Catalytic Michael addition reaction represents a fundamental importance in organic synthetic chem-istry.Whereas corresponding conversions toward intrinsically low reactive enamide remains an ongoing challenging.We herein report a copper-catalyzed conjugate addition of allenes to β-substituted alkenyl amides,one of the most challenging Michael acceptors.The present method utilizes readily available al-lenes as the latent carbon-based nucleophiles and simple,common β-substituted alkenyl amides as start-ing materials,unlike previous methods that usually preinstall an activating group to improve the reac-tivity of amide or uses highly reactive stoichiometric quantities of organometallics.Hence,this approach shows good functional group compatibility and can be implemented under mild reaction conditions with excellent level of chemo-and regioselectivities.

Key words

CuH catalysis/Allenes/Unsaturated amide/Conjugate addition/Regioselectivity

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基金项目

国家自然科学基金(22171042)

国家自然科学基金(21831002)

国家自然科学基金(22193012)

Jilin Province Natural science Foundation(20160520140JH)

中央高校基本科研业务费专项()

Ten Thousand Talents Program()

出版年

2024

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCDCSCD

影响因子：0.771

ISSN：1001-8417

参考文献量41

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