Iodine(III)-Initiated Bromoacetoxylation of Olefins

Hashem, Md. Abul; Jung, Alexander; Ries, Monika; Kirschning, Andreas

doi:10.1055/s-1998-1596

Cited by 52 publications

(25 citation statements)

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“…Kirschning and co-workers have developed several experimental procedures for the stereoselective bromoacetoxylation or iodoacetoxylation of alkenes based on the interaction of DIB with iodide or bromide anions 324,325. The actual reacting electrophilic species in these reactions are the diacetylhalogen(I) anions, (AcO) 2 I − and (AcO) 2 Br − , which can also be prepared as the polymer-supported variant 326–328.…”

Section: Iodine(iii) Compoundsmentioning

confidence: 99%

Chemistry of Polyvalent Iodine

2008

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Section: Iodine(iii) Compoundsmentioning

confidence: 99%

Chemistry of Polyvalent Iodine

2008

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“…The involvement of a stabilized anionic species [Br(O 2 CAr) 2 ] appeared less likely. Such species had previously been isolated and documented to constitute electrophilic bromine sources in stoichiometric alkene oxidation reactions . We generated such compounds by interaction between Bu 4 NBr and PIFA or PhI(O 2 CAr) 2 , respectively, as they are presumably produced under the conditions from Table , entries 4 and 5.…”

Section: Figurementioning

confidence: 99%

Designing Homogeneous Bromine Redox Catalysis for Selective Aliphatic C−H Bond Functionalization

et al. 2018

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The potential of homogeneous oxidation catalysis employing bromine has remained largely unexplored. We herein show that the combination of a tetraalkylammonium bromide and meta-chloroperbenzoic acid offers a unique catalyst system for the convenient and selective oxidation of saturated C(sp )-H bonds upon photochemical initiation with day light. This approach enables remote, intramolecular, position-selective C-H amination as demonstrated for 20 different examples. For the first time, an N-halogenated intermediate was isolated as the active catalyst state in a catalytic Hofmann-Löffler reaction. In addition, an expeditious one-pot synthesis of N-sulfonyl oxaziridines from N-sulfonamides was developed and exemplified for 15 transformations. These pioneering examples provide a change in paradigm for molecular catalysis with bromine.

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“…Where necessary, flash column chromatography was performed on silica gel 60 (230 ± 400 mesh). Except for alcohols 18,20,22,24,26,28,30,34,36, and 38 all starting compounds are commercially available. Alcohols 22, 24, and 26 were prepared from commercial (2R)-3-hydroxy-2-methylpropionic methyl ester by standard protection of the alcohol group and dibalpromoted reduction of the ester functionality under standard conditions.…”

Section: Methodsmentioning

confidence: 99%

Polymer‐Supported Bisacetoxybromate(I) Anion –‐An Efficient Co‐Oxidant in the TEMPO‐Mediated Oxidation of Primary and Secondary Alcohols

2003

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A polymer-bound reagent for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. The oxidation process is particular mild and allows one to prepare aldehydes with a-chirality without racemization. This also includes the synthesis of a-aminoaldehydes. In most cases, work-up of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. Insight into the role of the bromate(I) anion in the oxidation process was gained from the TEMPO-mediated oxidation of benzaldehyde in the presence of the hypochlorite anion loaded on an anion exchange resin.

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Iodine(III)-Initiated Bromoacetoxylation of Olefins

Cited by 52 publications

References 0 publications

Chemistry of Polyvalent Iodine

Chemistry of Polyvalent Iodine

Designing Homogeneous Bromine Redox Catalysis for Selective Aliphatic C−H Bond Functionalization

Polymer‐Supported Bisacetoxybromate(I) Anion –‐An Efficient Co‐Oxidant in the TEMPO‐Mediated Oxidation of Primary and Secondary Alcohols

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