2022
DOI: 10.1038/s41557-022-00913-4
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Direct conversion of white phosphorus to versatile phosphorus transfer reagents via oxidative onioation

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Cited by 43 publications
(18 citation statements)
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“…2 However, it is only very recently that it has finally become possible to successfully transform P 4 directly into a variety of useful P 1 products. 3 Moreover, and despite these extensive investigations, the number of successful examples remains extremely low, and those that do exist still suffer from substantial limitations. 4 As such, there remains a clear need to expand the range of strategies available for direct, productive P 4 activation, with new catalytic methods being particularly desirable.…”
mentioning
confidence: 99%
“…2 However, it is only very recently that it has finally become possible to successfully transform P 4 directly into a variety of useful P 1 products. 3 Moreover, and despite these extensive investigations, the number of successful examples remains extremely low, and those that do exist still suffer from substantial limitations. 4 As such, there remains a clear need to expand the range of strategies available for direct, productive P 4 activation, with new catalytic methods being particularly desirable.…”
mentioning
confidence: 99%
“…Whereas the latter strategy was based around the reduction of P 4 to a formal source of "P 3À " followed by reaction with electrophiles, Weigand et al have developed a formal oxidation of P 4 to give a "P 3 + " synthon, which can then undergo reaction with nucleophiles. [36] Specifically, the authors describe a strategy they term "oxidative onioation", which relies on reaction of P 4 with a suitable oxidizing Lewis acid and nitrogen-centred Lewis base. Using Ph 3 As(OTf) 2 and DMAP (4-dimethylaminopyridine) was found to result in formation of the highly electrophilic trication [(DMAP) 3 P] 3 + as a noncorrosive solid in excellent yield at multigram scale (Scheme 8a,…”
Section: Oxidative Onioation Of Pmentioning
confidence: 99%
“…The industrial method for the preparation of (EtO) 2 P(O)H is based on two environmentally toxic steps in which 1) P 4 is first chlorinated with dangerous molecular chlorine to generate PCl 3 ; 2) three equivalents of ethanol react with PCl 3 to give the desired product along with the releasing of one equivalent of EtCl and two equivalents of HCl [7] . However, this leads to obvious drawbacks such as toxic Cl 2 , strongly acidic conditions, hazardous and corrosive PCl 3 , and organo‐chloride waste (Scheme 1a) [8] . Furthermore, the use of molecular chlorine and PCl 3 suffers from poor selectivity and poor atom economy [9] …”
Section: Figurementioning
confidence: 99%
“…[7] However, this leads to obvious drawbacks such as toxic Cl 2 , strongly acidic conditions, hazardous and corrosive PCl 3 , and organo-chloride waste (Scheme 1a). [8] Furthermore, the use of molecular chlorine and PCl 3 suffers from poor selectivity and poor atom economy. [9] In order to avoid the use of Cl 2 and PCl 3 , the direct transformation of P 4 into (RO) 2 P(O)H is necessary.…”
mentioning
confidence: 99%