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Issue 19, 2018
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Base-promoted ring-closing carbonyl–allene metathesis for the synthesis of 2,4-disubstituted pyrroles

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Abstract

A base-promoted ring-closing carbonyl–allene metathesis reaction of N-allenyl β-enaminones (generated in situ from N-propargyl β-enaminones) gives 2,4-disubstituted pyrroles with cleavage of the C(sp)–C(sp3) bond. This transition metal-free procedure generates 1 equiv. of acetic acid as the sole byproduct. A preliminary mechanistic study supports a stepwise [2 + 2] cycloaddition/retro [2 + 2] reaction pathway.

Graphical abstract: Base-promoted ring-closing carbonyl–allene metathesis for the synthesis of 2,4-disubstituted pyrroles

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Publication details

The article was received on 28 May 2018, accepted on 30 Jul 2018 and first published on 30 Jul 2018


Article type: Communication
DOI: 10.1039/C8GC01675E
Green Chem., 2018,20, 4414-4417

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    Base-promoted ring-closing carbonyl–allene metathesis for the synthesis of 2,4-disubstituted pyrroles

    G. Cheng, W. Lv and L. Xue, Green Chem., 2018, 20, 4414
    DOI: 10.1039/C8GC01675E

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