Detailed Mechanistic Pattern in Halogen Dance Reactions of Iodothiophenes

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Author(s): Nader Sakhaee*, Sahar Sakhaee, Esmail Doustkhah, Akbar mobaraki

Journal Name: Current Organocatalysis

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Background: Synthetic chemists have utilized base catalyzed halogen dance reactions, ever since its discovery by Bunnet et al. Many modifications under various conditions have enabled synthetic chemists to build substituted hetero-cyclic targets with rich structural diversity.

Methods: Using DFT-Cam-B3LYP/ land2dz computations and focused on Hannes Frohlich et al. Halogen dance reac-tions of iodothiophenes, a new iodo-bridged transition state is proposed. This iodo-bridged TS was then used to put forth 8 possible isomerization as well as 8 possible disproportionation paths.

Results and Discussions: All mechanistic pathways were then thoroughly investigated based on TS’s energy and protona-tion/deprotonation steps to find the most suitable pathways. Collectively these mechanistic pathways were joined like a jigsaw puzzle to yield, for the first-time, a comprehensive cascade-like pattern for base-catalyzed halogen dance in io-dothiophenes.

Conclusion: The present work may well shed light on a dynamic domino mechanism which may well dominate the or-ganic chemistry of iodothiophenyl anions. Trends like this may reveal mechanistic pathways in base digestion of halogen-ated aromatic compounds in CS2.

Keywords: Substituted heterocyclic, base-catalyzed halogen dance, dynamic domino mechanisms, Iodothiophenes, cascadelike pattern, mechanistic pathways

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(E-pub Ahead of Print)
DOI: 10.2174/2213337207999201123195958
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