Chinese Journal of Organic Chemistry >
Nickel-Catalyzed Multicomponent Coupling of Butadiene, Aldehydes, Alkynes and Schwartz Reagent to Form 1,4-Dienes
Received date: 2021-01-13
Revised date: 2021-01-28
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(21690074); National Natural Science Foundation of China(21871288); National Natural Science Foundation of China(91856111); National Natural Science Foundation of China(21821002); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000)
The construction of skipped diene is a vital research area for organic synthesis, whose structure is found in many bioactive molecules. The synthesis of skipped diene from simple and readily available starting materials is highly desirable. Herein a nickel-catalyzed multicomponent coupling of 1,3-butadiene, aldehydes, alkynes, and Schwartz reagents for the preparation of skipped dienes is described. The reagents are common feedstock chemicals, especially 1,3-butadiene is an abundant feedstock produced from petroleum cracking. Moreover, the hydrozirconation of alkynes using Schwartz reagent was applied to in-situ prepared the alkenylzirconium reagents, which were used directly without further treatment. Various (E,E)-1,4-diene products were synthesized with excellent regio- and stereo-selectivity. The mild and straightforward reaction condition enables a broad substrate scope and good functional group tolerance. This protocol provides a useful and practical synthesis of skipped dienes.
Key words： skipped diene; nickel catalysis; butadiene; multicomponent reaction; coupling
Yu-Qing Li , Shi-Liang Shi . Nickel-Catalyzed Multicomponent Coupling of Butadiene, Aldehydes, Alkynes and Schwartz Reagent to Form 1,4-Dienes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 1939 -1948 . DOI: 10.6023/cjoc202101019
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