- LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)–H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates
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An efficient and mild method for the direct phosphorylation of phenols, alcohols, and amines with P(O)–H has been reported by LiI/TBHP mediated oxidative cross-coupling reaction. Moreover, this protocol extended to β-keto esters for the synthesis of enol phosphates using H-phosphonates. Notably, this developed method applied for the synthesis of organopesticides such as paraoxon, cyanophos, and methyl parathion. The key features of this protocol are mild conditions, short reaction time, good functional group tolerance, and broad substrate scope.
- Anitha, Thippani,Ashalu, Kashamalla Chinna,Sandeep, Mummadi,Mohd, Aabid,Wencel-Delord, Joanna,Colobert, Francoise,Reddy, Kallu Rajender
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p. 7463 - 7474
(2019/12/03)
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- Copper-catalyzed propargylation of diborylmethane
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A Cu/PPh3-catalyzed propargylic substitution reaction of diborylmethane is reported. Different substituted propargyl electrophiles can be employed in this reaction, and various synthetic valuable functional groups can be tolerated. Di-deuterate
- Li, Feng,Zhang, Zhen-Qi,Lu, Xi,Xiao, Bin,Fu, Yao
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supporting information
p. 3551 - 3554
(2017/03/31)
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- Copper(I)-catalyzed regio- and chemoselective single and double addition of nucleophilic silicon to propargylic chlorides and phosphates
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Copper(I)-catalyzed propargylic substitution of linear precursors with (Me2PhSi)2Zn predominantly yields the γ isomer independent of the propargylic leaving group. The thus formed allenylic silane reacts regioselectively with another equivalent of (Me2PhSi) 2Zn, yielding a bifunctional building block with allylic and vinylic silicon groups. The reaction rates of both steps are well-balanced for chloride (γ:α ≥ 99:1) where the propargylic displacement occurs quantitatively prior to the addition step. Substitutions of α-branched propargylic phosphates are also reported.
- Hazra, Chinmoy K.,Oestreich, Martin
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supporting information; experimental part
p. 4010 - 4013
(2012/10/08)
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- Copper(I)-catalyzed regioselective propargylic substitution involving Si-B bond activation
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The silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation allows several γ-selective propargylic substitutions. The regioselectivity (γ:α ratio) is strongly dependent on the propargylic leaving group. Chloride is superior to oxygen leaving groups in linear substrates (γ:α > 99:1), and it is only the phosphate group that also shows promising regiocontrol (γ:α = 90:10). That leaving group produces superb γ-selectivity (γ:α > 99:1) in α-branched propargylic systems, and enantioenriched substrates react with excellent central-to-axial chirality transfer.
- Vyas, Devendra J.,Hazra, Chinmoy K.,Oestreich, Martin
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supporting information; experimental part
p. 4462 - 4465
(2011/10/08)
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