Iodine(V) reagents in organic synthesis. Part 1. Synthesis of polycyclic heterocycles via Dess-Martin periodinane-mediated cascade cyclization: generality, scope, and mechanism of the reaction.

Iodine(V) reagents in organic synthesis. Part 1. Synthesis of polycyclic heterocycles via Dess-Martin periodinane-mediated cascade cyclization: generality, scope, and mechanism of the reaction. Nicolaou, K C, Montagnon, T, Baran, P S, Zhong, Y., & Sugita, K Journal of the American Chemical Society, 124(10):2245–58, March, 2002.

Paper abstract bibtex

o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form alpha,beta-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated by single electron transfer (SET) from the substrate to IBX to form a radical cation which reacts further to give the final products. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates, elevating the status of this reagent to that of a highly useful and chemoselective oxidant.

@article{Nicolaou2002,
	title = {Iodine({V}) reagents in organic synthesis. {Part} 1. {Synthesis} of polycyclic heterocycles via {Dess}-{Martin} periodinane-mediated cascade cyclization: generality, scope, and mechanism of the reaction.},
	volume = {124},
	issn = {0002-7863},
	url = {http://www.ncbi.nlm.nih.gov/pubmed/11878975 http://www.ncbi.nlm.nih.gov/pubmed/11878978},
	abstract = {o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form alpha,beta-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated by single electron transfer (SET) from the substrate to IBX to form a radical cation which reacts further to give the final products. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates, elevating the status of this reagent to that of a highly useful and chemoselective oxidant.},
	number = {10},
	journal = {Journal of the American Chemical Society},
	author = {Nicolaou, K C and Montagnon, T and Baran, P S and Zhong, Y-L and Sugita, K},
	month = mar,
	year = {2002},
	pmid = {11878975},
	keywords = {\#nosource, Anilides, Anilides: chemistry, Heterocyclic Compounds, Heterocyclic Compounds: chemical synthesis, Hydrogenation, Iodine, Iodine: chemistry, Iodobenzoates, Iodobenzoates: chemistry, Oxazines, Oxazines: chemistry, Oxidation-Reduction, Polycyclic Compounds, Polycyclic Compounds: chemical synthesis, Urea, Urea: chemistry, Urethane, Urethane: chemistry},
	pages = {2245--58},
}

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