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Synlett 2000; 2000(4): 475-478
DOI: 10.1055/s-2000-6577
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Observations on the Enforced Orthogonality Concept for the Synthesis of Fully Hindered Biaryls by a Tin-Free Intramolecular Radical Ipso Substitution

Eric Bonfand* , Linnea Forslund, William B. Motherwell, Santiago Vázquez
  • *Department of Chemistry, Christopher Ingold Laboratories, University College London, 20 Gordon Street, London WC1H 0AJ, UK; Fax +44-1 71 3 80 75 24; E-mail: w.b.motherwell@ucl.ac.uk
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Publication Date:
31 December 2000 (online)

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Hindered biaryls have been simply prepared using diazonium salt precursors and an intramolecular free radical [1,5] ipso substitution protocol. The introduction of an additional substituent ortho to the diazonium group in the σ aryl radical donor further enforces the formation of ipso substitution products and hence fully hindered biaryls are the favoured products.

radical reactions - biaryls - titanium trichloride - substituent effects - ipso substitution