Organocatalysis by Neutral Multidentate Halogen‐Bond Donors

Florian Kniep, Stefan H. Jungbauer, Qi Zhang, Sebastian M. Walter, S. Schindler, Ingo Schnapperelle, Eberhardt Herdtweck, Stefan M. Huber

Angewandte Chemie International Edition · 2013 · 300 citations · 57 references

Concepts

Abstract

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.

References

57