Jump to main content
Jump to site search

Issue 33, 2019
Previous Article Next Article

An organocatalytic method for constructing pyrroles via the cycloisomerisation of Z-1-iodo-4-N-methylbenzenesulfonyl-1,6-enynes

Author affiliations

Abstract

A new cycloisomerisation of Z-1-iodo-4-N-methylbenzenesulfonyl-1,6-enynes to functionalized pyrroles was realized in the presence of an organomolecule (4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine) and KOtBu. The transformations were performed efficiently to produce different kinds of functionalized pyrroles within 10 min. This is the first example of an organomolecule promoted methodology with vinyl iodides from a non-aromatic system to an aromatic system, which offers an excellent option toward establishing a new horizon for cross-coupling reactions of vinyl halides. Preliminary mechanistic studies were performed and a crude radical pathway was proposed.

Graphical abstract: An organocatalytic method for constructing pyrroles via the cycloisomerisation of Z-1-iodo-4-N-methylbenzenesulfonyl-1,6-enynes

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 May 2019, accepted on 15 Jul 2019 and first published on 16 Jul 2019


Article type: Communication
DOI: 10.1039/C9OB01123D
Org. Biomol. Chem., 2019,17, 7669-7673

  •   Request permissions

    An organocatalytic method for constructing pyrroles via the cycloisomerisation of Z-1-iodo-4-N-methylbenzenesulfonyl-1,6-enynes

    L. Meng, X. Chi, X. Sun, C. Cao, B. Ai, Q. Liu, P. Zhao, Z. Zhao, Y. Dong and H. Liu, Org. Biomol. Chem., 2019, 17, 7669
    DOI: 10.1039/C9OB01123D

Search articles by author

Spotlight

Advertisements