38828-07-8Relevant academic research and scientific papers
Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Olefins with α-Heteroatom Phosphorus or Sulfur Alkyl Electrophiles
Fu, Yao,He, Shi-Jiang,Li, Yan,Lu, Xi,Wang, Jia-Wang,Wang, Xiao-Xu,Xu, Zhe-Yuan
supporting information, (2020/01/22)
Substantial advances in enantioconvergent C(sp3)-C(sp3) bond formation reactions have been made in recent years through the use of transition-metal-catalyzed cross-coupling reactions of racemic secondary alkyl electrophiles with organometallic reagents. Herein, we report a general process for the asymmetric construction of alkyl-alkyl bonds adjacent to heteroatoms, namely, a nickel-catalyzed enantioconvergent reductive hydroalkylation of olefins with α-heteroatom phosphorus or sulfur alkyl electrophiles. Including the use of readily available olefins, this reaction has considerable advantages, such as mild reaction conditions, a broad substrate scope, and good functional group compatibility, making it a desirable alternative to traditional electrophile-nucleophile cross-coupling reactions.
Selective C-P(O) Bond Cleavage of Organophosphine Oxides by Sodium
Zhang, Jian-Qiu,Ikawa, Eiichi,Fujino, Hiroyoshi,Naganawa, Yuki,Nakajima, Yumiko,Han, Li-Biao
, p. 14166 - 14173 (2020/11/13)
Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). The destiny of PhNa co-generated is disclosed. A series of alkyl halides R4X and aryl halides ArX all react with Ph2P(ONa) to produce the corresponding phosphine oxides in good to excellent yields.
Ambident reactivity of chloro(dialkylamino)-(diphenylphosphinoyl)methanes
Morgalyuk, Vasilii Petrovich,Strelkova, Tat'Yana Vladimirovna,Nifant'Ev, Eduard Eugenievich
supporting information; experimental part, p. 93 - 100 (2012/03/07)
The chemical properties of chloro(dialkylamino)(diphenylphosphinoyl) methanes have been studied using the simplest compound of this series, chloro(dimethylamino)(diphenylphosphinoyl)methane, as an example. Chloro- (dimethylamino)(diphenylphosphinoyl)methane shows ambident reactivity when reacting with electrophiles and nucleophiles depending on coreactant nature, it behaves as either electrophilic substrate or phosphorus nucleophile. This fact can be explained by its dissociation in solutions with both C-Cl bond cleavage to give (dimethylamino)- (diphenylphosphinoyl)methyl cation and Cl- anion and C-P bond cleavage to form chloro(dimethylamino)methyl cation and diphenylphosphinite anion. The capability of chloro(dimethylamino) (diphenylphosphinoyl)methane to produce spontaneously Ph2PO-anion allows us to recommend application in organic and organophosphorus synthesis as a synthetic equivalent (synthon) of diphenylphosphinite anion.
Synthesis of (±)-(15E)&(15Z)-16-oxa-2,3-oxidosqualenes
Park, Jeongho,Min, Changhee,Williams, Howard,Scotf
, p. 5719 - 5722 (2007/10/02)
As potential inhibitors of oxidosqualene cyclase (OSC) (±)-(15E)&(15Z)-16-oxa-2,3-oxidosqualenes ((9)&(10)) were synthesized by the Wittig-Horner reaction from diphenylphosphinoyl-1-ethyl-geranyl ether (5) and the epoxy aldehyde (6). An efficient synthetic method for the Wittig-Horner reagent (5) was developed.
