Triarylmethanes and their Medium-Ring Analogues by Unactivated Truce-Smiles Rearrangement of Benzanilides

Roman Abrams, Mehul H Jesani, Alex Browning, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

5 Citations (Scopus)
43 Downloads (Pure)

Abstract

Intramolecular nucleophilic aromatic substitution (Truce-Smiles rearrangement) of the anions of 2-benzyl benzanilides leads to triarylmethanes in an operationally simple manner. The reaction succeeds even without electronic activation of the ring that plays the role of electrophile in the SNAr reaction, being accelerated instead by the preferred conformation imposed by the tertiary amide tether. The amide substituent of the product may be removed or transformed into alternative functional groups. A ring-expanding variant (n to n + 4) of the reaction provided a route to doubly benzo-fused medium ring lactams of 10 or 11 members. Hammett analysis returned a r value consistent with the operation of a partially concerted reaction mechanism.
Original languageEnglish
Pages (from-to)11272-11277
Number of pages6
JournalAngewandte Chemie - International Edition
Volume60
Issue number20
Early online date8 Apr 2021
DOIs
Publication statusPublished - 10 May 2021

Bibliographical note

Funding Information:
The work was supported by the EPSRC Centre for Doctoral Training in Catalysis and the EPSRC Centre for Doctoral Training in Technology Enhanced Chemical Synthesis.

Publisher Copyright:
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

Structured keywords

  • BCS and TECS CDTs

Keywords

  • Hammett plot
  • medium ring
  • SNAr
  • triarylmethane
  • Truce–Smiles rearrangement

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