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Selective Synthesis of Multifunctionalized 2,3-Dihydroinden-1-ones and 1,3-Dihydroisobenzofurans from the Reaction of <i>o</i>‑Alkynylbenzaldehydes with Imines Steered by N‑Heterocyclic Carbene/Copper(II) and N‑Heterocyclic Carbene/Base Cascade Catalysis

By Ya-Li Ding (3341462), Shi-Ning Li (3341465) and Ying Cheng (288456)

Abstract

We report in this paper the N-heterocyclic carbene/transition metal and N-heterocyclic carbene/base cascade catalysis in the reaction of <i>o</i>-alkynylbenzaldehydes with <i>N</i>-acylimines, demonstrating the example of reaction pathways steered by catalysts. Under the catalysis of a thiazole carbene/Et<sub>3</sub>N followed by Cu­(OAc)<sub>2</sub> in acetonitrile at ambient temperature, <i>o</i>-alkynylbenzaldehydes underwent reaction with <i>N</i>-acylimines that were generated in situ from <i>N</i>-((aryl)­(tosyl)­methyl)­amides to produce a pair of <i>Z</i>- and <i>E</i>-2-amido-3-benzylidene-1-indanones in 47–92% total yields. The reaction of the same substrates in the presence of a thiazole carbene and Cs<sub>2</sub>CO<sub>3</sub>, on the other hand, afforded (1<i>E</i>,3<i>Z</i>)-1-amidobenzylidene-3-benzylidene-1,3-dihydroisobenzofurans in 54–89% yields

Topics: Biochemistry, Genetics, Molecular Biology, Inorganic Chemistry, Infectious Diseases, Computational Biology, Environmental Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, thiazole carbene, Imines Steered, ambient temperature, Carbene, acylimine, catalysi, reaction pathways, E -2- amido -3-benzylidene, yield, alkynylbenzaldehyde, Cs 2 CO 3, Selective Synthesis, N-heterocyclic
Year: 2018
DOI identifier: 10.1021/acs.joc.8b01163.s002
OAI identifier: oai:figshare.com:article/6621473
Provided by: FigShare
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