Preparation and in situ use of unstable N-alkyl a-diazo-g-butyrolactams in RhII-catalyzed X-H insertion reactions

  1. Maria Eremeyeva,
  2. Daniil Zhukovsky,
  3. Dmitry Dar'inORCID Logo and
  4. Mikhail KrasavinORCID Logo

Submitting author affiliation: Saint Petersburg State University, Peterhof, Russian Federation

Beilstein Arch. 2020, 202015. doi:10.3762/bxiv.2020.15.v1

Published 07 Feb 2020

  • Preprint


N-Alkyl a-diazo-g-butyrolactams previously found to be unstable and undergo unproductive dimerization to bis-hydrazones, were successfully converted immediately to various X-H insertion products with alcohols, aromatic amines and thiols via an in situ RhII-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reaction tends to yield enamine adducts.

Keywords: N-alkyl 2-pyrrolidones; in situ reaction; stability of diazo compounds; RhII-catalyzed insertion reactions

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Eremeyeva, M.; Zhukovsky, D.; Dar'in, D.; Krasavin, M. Beilstein Arch. 2020, 202015. doi:10.3762/bxiv.2020.15.v1

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