Chemistry of organophosphorus compounds containing the peroxide bond

Konieczny, M.; Sosnovsky, George

doi:10.1021/cr00041a003

Cited by 10 publications

(5 citation statements)

References 28 publications

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“…[9e] In contrast to common redox-neutral phosphatation reactions,a nalogous oxidative strategies in which non-activated hydrocarbons,s uch as alkenes,s erve as reaction partners for phosphate donor reagents have thus far been limited to perphosphoric esters. [10,11] Thee xtensive body of efforts towards the synthesis and application of phosphate esters clearly emphasizes the significance of efficient, mild, and site-selective methods for their construction and underscores the increasing demand for innovative and complementary catalytic phosphatation concepts.…”

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confidence: 99%

Photocatalytic Aerobic Phosphatation of Alkenes

et al. 2018

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A catalytic regime for the direct phosphatation of simple, non-polarized alkenes has been devised that is based on using ordinary, non-activated phosphoric acid diesters as the phosphate source and O as the terminal oxidant. The title method enables the direct and highly economic construction of a diverse range of allylic phosphate esters. From a conceptual viewpoint, the aerobic phosphatation is entirely complementary to traditional methods for phosphate ester formation, which predominantly rely on the use of prefunctionalized or preactivated reactants, such as alcohols and phosphoryl halides. The title transformation is enabled by the interplay of a photoredox and a selenium π-acid catalyst and involves a sequence of single-electron-transfer processes.

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confidence: 99%

Photocatalytic Aerobic Phosphatation of Alkenes

et al. 2018

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“…Peroxyphosphates, for example (EtO) 2 P(O)OO t Bu, (which is shown in Figure ) are more labile than peresters but can often be prepared by relatively similar methods and have been reviewed in detail . Like peresters, they are strong electrophiles; reaction of a Grignard reagent with diethyl tert ‐butyl peroxyphosphate gives a good yield of the tert ‐butyl ether .…”

Section: Related Compoundsmentioning

confidence: 99%

The Chemistry of Peresters

Locklear

Dussault

2020

Eur J Org Chem

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“…Although the peroxyphosphorus intermediate R2P(O)OO-has been postulated as a possible intermediate in certain biological transformations, it has neither been isolated nor its presence confirmed. 8 We have now found that phenylphosphonic dichloride reacted with superoxide (02*-) at -4 "C in acetonitrile to form a peroxyphosphorus intermediate which shows strong oxidizing ability and converts various aryl and alkyl thioamides into the correspnding amides in excellent yields.…”

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confidence: 96%