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Organocatalysis by Neutral Multidentate Halogen‐Bond Donors
Author(s) -
Kniep Florian,
Jungbauer Stefan H.,
Zhang Qi,
Walter Sebastian M.,
Schindler Severin,
Schnapperelle Ingo,
Herdtweck Eberhardt,
Huber Stefan M.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301351
Subject(s) - halogen , organocatalysis , chemistry , denticity , lewis acids and bases , halogen bond , ketene , silylation , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , enantioselective synthesis , crystal structure , alkyl
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.