Iodine(V) Reagents in Organic Synthesis. Part 3. New Routes to Heterocyclic Compounds via o-Iodoxybenzoic Acid-Mediated Cyclizations: Generality, Scope, and Mechanism. Nicolaou, K C, Baran, P S, Zhong, Y., Barluenga, S, Hunt, K W, Kranich, R, & a Vega, J Journal of the American Chemical Society, 124(10):2233–44, March, 2002. abstract bibtex The discovery and development of the o-iodoxybenzoic acid (IBX) reaction with certain unsaturated N-aryl amides (anilides) to form heterocycles are described. The application of the method to the synthesis of delta-lactams, cyclic urethanes, hydroxy amines, and amino sugars among other important building blocks and intermediates is detailed. In addition to the generality and scope of this cyclization reaction, this article describes a number of mechanistic investigations suggesting a single electron transfer from the anilide functionality to IBX and implicating a radical-based mechanism for the reaction.
@article{Nicolaou2002,
title = {Iodine({{V}}) Reagents in Organic Synthesis. {{Part}} 3. {{New}} Routes to Heterocyclic Compounds via o-Iodoxybenzoic Acid-Mediated Cyclizations: Generality, Scope, and Mechanism.},
author = {Nicolaou, K C and Baran, P S and Zhong, Y-L and Barluenga, S and Hunt, K W and Kranich, R and a Vega, J},
year = {2002},
month = mar,
journal = {Journal of the American Chemical Society},
volume = {124},
number = {10},
eprint = {11878977},
eprinttype = {pubmed},
pages = {2233--44},
issn = {0002-7863},
abstract = {The discovery and development of the o-iodoxybenzoic acid (IBX) reaction with certain unsaturated N-aryl amides (anilides) to form heterocycles are described. The application of the method to the synthesis of delta-lactams, cyclic urethanes, hydroxy amines, and amino sugars among other important building blocks and intermediates is detailed. In addition to the generality and scope of this cyclization reaction, this article describes a number of mechanistic investigations suggesting a single electron transfer from the anilide functionality to IBX and implicating a radical-based mechanism for the reaction.},
pmid = {11878977},
keywords = {\#nosource,Amines,Amines: chemical synthesis,Amino Sugars,Amino Sugars: chemical synthesis,Anilides,Anilides: chemistry,Heterocyclic Compounds,Heterocyclic Compounds: chemical synthesis,Iodobenzoates,Iodobenzoates: chemistry,Lactams,Lactams: chemical synthesis,Urethane,Urethane: chemical synthesis}
}
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