ChemInform Abstract: Nucleophile‐Selective Cross‐Coupling Reactions with Vinyl and Alkynyl Bromides on a Dinucleophilic Aromatic Substrate.

Abstract

Substrate. -A nucleophile-selective cross--coupling reaction of dinucleophilic thiophene (I) with vinyl and alkynyl bromides is developed, extending the scope of electrophiles usable in Sonogashira-or Heck-type coupling reactions. This reversal of the roles of the coupling partners represents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group and subsequent Suzuki-Miyaura cross-coupling reactions can be carried out to provide difunctionalized thiophenes in a one-pot manner. -(HE, L.-Y.; SCHULZ-SENFT, M.; THIEDEMANN, B.; LINSHOEFT, J.; GATES, P. J.; STAUBITZ*, A.; Eur. J. Org. Chem. 2015, 11, 2498-2502, http://dx.