4.7 Article

Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism

Journal

CHEMICAL COMMUNICATIONS
Volume 48, Issue 66, Pages 8249-8251

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc33547f

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Funding

  1. Universite de Montreal
  2. Natural Science and Engineering Council of Canada (NSERC)
  3. Canada Research Chair Program
  4. Canada Foundation for Innovation
  5. NSERC

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A variety of polycycles can be synthesized via an intramolecular alkylation cyclization promoted by Ni(PPh3)(4) and NaHMDS. Mechanistic investigations support the catalytic nature of Ni-0 in the course of TEMPO scavenging experiments and its association with the substrate and NaHMDS to form an adduct by DOSY NMR.

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