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Synlett 2000; 2000(8): 1127-1128
DOI: 10.1055/s-2000-6751
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Selective Functionalization of an Isodurene-Cr(CO)3 Complex

M. F. Semmelhack* , Gerhard Hilt
  • *Department of Chemistry, Princeton University, Princeton, NJ 08544, USA; Fax 609-258-34 09; E-mail: mfshack@princeton.edu
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Publication Date:
31 December 2000 (online)

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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.

metallation - organometallic chemistry - arene complexes - regioselectivity

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