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Redox‐Neutral Rhodium‐Catalyzed [4+1] Annulation through Formal Dehydrogenative Vinylidene Insertion
Author(s) -
Liu Huan,
Song Shengjin,
Wang ChengQiang,
Feng Chao,
Loh TeckPeng
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201601341
Subject(s) - annulation , rhodium , chemistry , catalysis , stereospecificity , bond cleavage , combinatorial chemistry , methylene , organic chemistry
A synthetic protocol for the expedient construction of 5‐methylene‐1 H ‐pyrrol‐2(5 H )‐one derivatives through rhodium‐catalyzed [4+1] annulation with gem ‐difluoroacrylate as the C 1 component was reported. By taking advantage of the twofold C−F bond cleavage occurring during the annulation, this reaction not only allows the synthesis of these heterocyclic compounds under overall oxidant‐free conditions but also renders the transformation stereospecific. The very mild reaction conditions employed ensure compatibility with a wide variety of synthetically useful functional groups.