Skip to Main content Skip to Navigation
Journal articles

The bio-based methyl coumalate involved Morita–Baylis–Hillman reaction

Abstract : We report the first use of renewable, bio-based, non-hazardous feedstock methyl coumalate (MC) in organocatalyzed Morita–Baylis–Hillman (MBH) reactions. This atom-economical pathway employs inexpensive Et3N as a catalyst in ethanol. Synthon MC efficiently constructs C–C bonds with various imines and aldehydes in moderate to good yields. This catalytic process is triggered via an unprecedented 1,6-conjugated addition, as opposed to the classical MBH reaction. Moreover, this methodology expands Morita–Baylis–Hillman donor capabilities to a 2-pyrone derivative for the first time. MBH adducts described herein could be applied to the synthesis of fine chemicals with biologically active structural cores, such as diphenylmethanol, hydroisobenzofurans, and hydroisoindoles.
Document type :
Journal articles
Complete list of metadatas

Cited literature [58 references]  Display  Hide  Download
Contributor : Hal Sorbonne Université Gestionnaire <>
Submitted on : Wednesday, July 10, 2019 - 12:42:57 PM
Last modification on : Tuesday, July 21, 2020 - 3:06:01 AM


Bio-based methyl coumalate.pdf
Files produced by the author(s)



Liang Chang, Serge Thorimbert, Luc Dechoux. The bio-based methyl coumalate involved Morita–Baylis–Hillman reaction. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2019, 17 (10), pp.2784-2791. ⟨10.1039/C9OB00328B⟩. ⟨hal-02178990⟩



Record views


Files downloads