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The Enones as New Alkenyl Reagents via Ligand Promoted C–C Bonds Activation

preprint
submitted on 05.03.2021, 01:53 and posted on 05.03.2021, 13:09 by Hanyuan Li, Mei-Ling Wang, Yue-Wen Liu, Ling-Jun Li, Hui Xu, Huixiong Dai
Complementary to C–H bond activation, C–C bond activation has emerged over the past few years as an increasingly powerful tool to access and modify complex molecules. Ketones, owing to their versatility and availability, provide a significant platform for C–C bond activating reactions. Herein, we reported a β-carbon elimination strategy for alkene(sp2)–C(O) bonds to realize the olefination of unstrained enones via a vinyl palladium species, which delivers a series of conjugated polyene compounds. The protocol features broad substrate scope, excellent functional group tolerance and can be extended to dba (dibenzylideneacetone) substrates for olefination, alkynylation, arylation and amination, which demonstrates the generality of the approach and affords two valuable products in one pot. Furthermore, the late-stage functionalization of natural products (β-ionone and acetyl cedrene) and synthesis of natural products (piperine, lignarenone, novenone) highlight the potential utility of the reaction.

History

Email Address of Submitting Author

hxdai@simm.ac.cn

Institution

Shanghai Institute of Materia Medica

Country

China

ORCID For Submitting Author

0000-0002-2937-6146

Declaration of Conflict of Interest

The authors declare no competing interests.

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