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Organocatalysis by Neutral Multidentate Halogen‐Bond Donors
299
Citations
57
References
2013
Year
HalogenationNovel OrganocatalystsEngineeringBiochemistryNatural SciencesOrganic ChemistryHalogen-based Lewis AcidsCatalysisKetene Silyl AcetalsChemistryIodine SubstituentsAsymmetric Catalysis
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.
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