Facile Preparation of 2-Iodophenyl Trifluoromethanesulfonates: Superior Aryne Precursors

Facile Preparation of 2-Iodophenyl Trifluoromethanesulfonates: Superior Aryne Precursors

Abstract A comparative study of 3-methoxyaryne precursors ­revealed 2-iodo-3-methoxyphenyl triflate as the most effective in nonpolar solvent. Use of Hoppe’s N-isopropyl carbamate allows for the systematic preparation of a variety of 2-iodophenyl triflates via a ­directed ORTHO-lithiation-iodination...

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Veröffentlicht in:Synlett 2007-09, Vol.2007 (14), p.2227-2231
Hauptverfasser: Ganta, Ashok, Snowden, Timothy S.
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract A comparative study of 3-methoxyaryne precursors ­revealed 2-iodo-3-methoxyphenyl triflate as the most effective in nonpolar solvent. Use of Hoppe’s N-isopropyl carbamate allows for the systematic preparation of a variety of 2-iodophenyl triflates via a ­directed ORTHO-lithiation-iodination-decarbamation sequence. These steps are possible without isolation of the intermediate ­iodophenyl carbamates.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-985565