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Mechanisms in Iodine Catalysis
Author(s) -
Breugst Martin,
von der Heiden Daniel
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201706136
Subject(s) - catalysis , aldol reaction , chemistry , lewis acids and bases , lewis acid catalysis , iodine , halogen , organic chemistry , acid catalysis , combinatorial chemistry , alkyl
Molecular iodine has been used for more than 100 years as a remarkable catalyst for many organic transformations such as cycloadditions, Michael and aldol reactions, or esterifications. Different explanations for the origin of its catalytic effect have been proposed in the last decades including a “hidden” Brønsted acid catalysis by HI, a Lewis‐acid (or halogen‐bond) activation, or catalysis by an iodonium(I) species. Recently, iodine catalysis again gained more interest due to the latest developments in halogen‐bond catalysis. In this Minireview, we first summarize the experimental basis for the proposed modes of activation. Subsequently, we analyze typical iodine‐catalyzed reactions to gain more insights into the underlying reaction mechanisms.