Selective oxidation at carbon adjacent to aromatic systems with IBX.

  title={Selective oxidation at carbon adjacent to aromatic systems with IBX.},
  author={Kyriacos C Nicolaou and Phil S. Baran and Yong-Li Zhong},
  journal={Journal of the American Chemical Society},
  volume={123 13},
Recei Ved December 5, 2000 A number of new synthetic technologies based on the reactivity of the periodinane reagents DMP and IBX have recently been reported from these laboratories. 1 These reactions include the IBXinduced cyclization of unsaturated anilides (Figure 1A), 1b whose single-electron transfer (SET) mechanism was recently elucidated, 2 and the introduction of unsaturation next to carbonyl groups, 1d now also believed to proceed, by analogy, via a SET mechanism (Figure 1B). On the… 

Figures and Tables from this paper

Modulation of the Reactivity Profile of IBX by Ligand Complexation: Ambient Temperature Dehydrogenation of Aldehydes and Ketones to α,β‐Unsaturated Carbonyl Compounds
We have recently reported[1, 2] that the use of IBX (oiodoxybenzoic acid)[3] represents a highly adept method for accessing the coveted, yet synthetically challenging, , unsaturated carbonyl motif by
New synthetic approach for the construction of multisubstituted 2-acyl furans by the IBX-mediated cascade oxidation/cyclization of cis-2-En-4-yn-1-ols (IBX=2-iodoxybenzoic acid).
This paper reports for the first time of IBX-promoted cascade oxidation/cyclization of cis2-en-4-yn-1-ols, which represents an efficient and diversity oriented protocol for the convergent construction of substituted 2-acyl furans.
New Site‐Selective Organoradical Based on Hypervalent Iodine Reagent for Controlled Alkane sp3 CH Oxidations
Oxidation is an important transformation and is involved in many industrial pharmaceutical and fine chemical syntheses for functional group conversions and for producing bondforming events. With the
Site-selective electrooxidation of methylarenes to aromatic acetals
An electrochemical, site-selective method for the oxidation of methyl benzoheterocycles to aromatic acetals without using chemical oxidants or transition metal catalysts is shown.
Oxidation Catalysis by an Aerobically Generated Dess-Martin Periodinane Analogue.
In this work, aerobic oxidation of iodobenzenes is coupled with disproportionation of the initially generated I(III) compounds to generate I(V) reagents, which exhibit substrate oxidation chemistry analogous to that of DMP.
Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation.
The introduction of alkynes by using ethynylbenziodoxol(on)e (EBX) reagents has been highly successful and their use to construct carbon-heteroatom and carbon-carbon bonds will be presented.
Synthesis of Benzylic Alcohols by C–H Oxidation
This work reports the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant, and attempts to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity.
Selective benzylic C–H monooxygenation mediated by iodine oxides
A preliminary mechanistic analysis suggests that this NHPI-iodate system is functioning by a radical-based mechanism where iodine generated in situ captures formed benzylic radicals.
Oxidative cleavage of vicinal diols: IBX can do what Dess-Martin periodinane (DMP) can.
The fact that IBX exhibits reactivity akin to DMP is demonstrated from the results observed with strained and sterically hindered syn 1,2-diols, which undergo oxidative cleavage via a 12-I-5