Selective functionalization of an isodurene-Cr(CO)3 complex

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Abstract

Two synthesis routes to thiol 1 from mesitylene were evaluated. A direct bromination of a 1,2,3,5-tetraalkylbenzene derivative (2) was relatively unselective and gave the desired bromide in 10% yield. Deprotonation of the corresponding Cr(CO)3 complex with LiTMP and trapping with a bulky silane (Ph2tBuSiCl) gave high selectivity for the desired position, apparently through equilibration of benzylic anions and a product-determining trapping step.

Original languageEnglish (US)
Pages (from-to)1127-1128
Number of pages2
JournalSynlett
Issue number8
StatePublished - Sep 4 2000

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Keywords

  • Arene complexes
  • Metallation
  • Organometallic chemistry
  • Regioselectivity

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