On the mechanism of the Shapiro reaction: Understanding the regioselectivity

  1. Funes-Ardoiz, I. 1
  2. Losantos, R. 1
  3. Sampedro, D. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Journal:
RSC Advances

ISSN: 2046-2069

Year of publication: 2015

Volume: 5

Issue: 47

Pages: 37292-37297

Type: Article

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DOI: 10.1039/C5RA05141J SCOPUS: 2-s2.0-84928975683 WoS: WOS:000353653200018 GOOGLE SCHOLAR

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Abstract

A detailed DFT-level mechanism elucidation of the two-step reaction of tosylhydrazones with alkyllithium reagents (the Shapiro reaction) is presented. A rationale of the experimental regioselectivity is offered together with some suggestions for modifying the experimental main regioisomer. Also, the proposed general mechanism was checked with a recent modification of the Shapiro reaction involving a fluorination reaction. © 2015 The Royal Society of Chemistry.