An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes as C4 units

Chengzhou Jiang; Jiamin Wu; Jiabin Han; Kai Chen; Yang Qian; Zhengyu Zhang; Yaojia Jiang

doi:10.1039/D1CC01254A

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An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes as C₄ units†

Chengzhou Jiang,^a Jiamin Wu,^a Jiabin Han,^a Kai Chen,^b Yang Qian,^a Zhengyu Zhang^a and Yaojia Jiang

*^ab

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* Corresponding authors

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, China
E-mail: iamyjjiang@njtech.edu.cn

^b Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi, Guiyang 550025, China

Abstract

An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the C [double bond, length as m-dash] C bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standard C₄ units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a C [double bond, length as m-dash] C bond cleavage of the enaminone and insertion of a new C(sp²) source with the formation of two C–C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.

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Article information

DOI: https://doi.org/10.1039/D1CC01254A
Article type: Communication
Submitted: 08 Mar 2021
Accepted: 30 Apr 2021
First published: 01 May 2021

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Chem. Commun., 2021,57, 5710-5713

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An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes as C₄ units

C. Jiang, J. Wu, J. Han, K. Chen, Y. Qian, Z. Zhang and Y. Jiang, Chem. Commun., 2021, 57, 5710 DOI: 10.1039/D1CC01254A

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Chemical Communications