Iodine(V) reagents in organic synthesis. Part 3. New routes to heterocyclic compounds via o-iodoxybenzoic acid-mediated cyclizations: generality, scope, and mechanism.
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.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Baran
P S
PS
Zhong
Y-L
YL
Barluenga
S
S
Hunt
K W
KW
Kranich
R
R
Vega
J A
JA
D000588:Amines / Q000138:chemical synthesis; D000606:Amino Sugars / Q000138:chemical synthesis; D000813:Anilides / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis; D014520:Urethane / Q000138:chemical synthesis
D000588:Amines; D000606:Amino Sugars; D000813:Anilides; D006571:Heterocyclic Compounds; D007462:Iodobenzenes; D007463:Iodobenzoates; D007769:Lactams; D014520:Urethane; C476101:o-iodoxybenzoic acid