Organocatalysis by Neutral Multidentate Halogen-Bond Donors

Authors


  • Our research is funded by the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft, the Leonhart Lorenz Foundation, and the Dr. Otto Röhm Gedächtnisstiftung. We thank Florian Mayr, Tobias Kapp, and Olaf Ackermann for experimental contributions. We also thank Prof. Dr. Thorsten Bach for continuing support.

Abstract

original image

I(n)organocatalysis: Neutral multidentate halogen-bond donors (halogen-based Lewis acids) catalyze the reaction of 1-chloroisochroman with ketene silyl acetals. The organocatalytic activity is linked to the presence (and number as well as orientation) of iodine substituents. As hidden acid catalysis can be ruled out with high probability, this case constitutes strong evidence for halogen-bond based organocatalysis. TBS=tert-butyldimethylsilyl.

Ancillary