16933-43-0Relevant academic research and scientific papers
Electrochemical Dehydrogenative Coupling of Alcohols with Hydrogen Phosphoryl Compounds: A Green Protocol for P?O Bond Formation
Li, Qian-Yu,Swaroop, Toreshettahally R.,Hou, Cheng,Wang, Zi-Qiang,Pan, Ying-Ming,Tang, Hai-Tao
, p. 1761 - 1765 (2019)
This study reports the environment-friendly electrochemical transformation of structurally diverse phosphorus compounds and alcohol into phosphonates in the presence of ammonium iodide as electrolyte and redox catalyst in acetonitrile at ambient temperature. This method for P?O bond formation exhibits remarkable features, such as transition metal- and oxidant-free conditions. A reliable mechanism is proposed after control and cyclic voltammetry experiments. (Figure presented.).
Tf2O/DMSO-Promoted P-O and P-S Bond Formation: A Scalable Synthesis of Multifarious Organophosphinates and Thiophosphates
Shen, Jian,Li, Qi-Wei,Zhang, Xin-Yue,Wang, Xue,Li, Gui-Zhi,Li, Wen-Zuo,Yang, Shang-Dong,Yang, Bin
supporting information, p. 1541 - 1547 (2021/04/05)
A Tf2O/DMSO-based system for the dehydrogenative coupling of a wide range of alcohols, phenols, thiols, and thiophenols with diverse phosphorus reagents has been developed. This metal- and strong-oxidant-free strategy provides a facile approach to a great variety of organophosphinates and thiophosphates. The simple reaction system, good functional-group tolerance, and broad substrate scope enable the application of this method to the modification of natural products and the direct synthesis of bioactive molecules and flame retardants.
Iron-catalyzed clean dehydrogenative coupling of alcohols with P(O)-H compounds: A new protocol for ROH phosphorylation
Li, Chunya,Chen, Tieqiao,Han, Li-Biao
supporting information, p. 14893 - 14897 (2016/10/11)
An efficient oxygen-phosphoryl bond-forming reaction via iron-catalyzed cross dehydrogenative coupling has been developed. This transformation proceeds efficiently under oxidant- and halide-free reaction conditions with H2 liberation, and represents a straightforward method to prepare valuable organophosphoryl compounds from the readily available alcohols and P(O)-H compounds.
Efficient asymmetric synthesis of structurally diverse p-stereogenic phosphinamides for catalyst design
Han, Zhengxu S.,Zhang, Li,Xu, Yibo,Sieber, Joshua D.,Marsini, Maurice A.,Li, Zhibin,Reeves, Jonathan T.,Fandrick, Keith R.,Patel, Nitinchandra D.,Desrosiers, Jean-Nicolas,Qu, Bo,Chen, Anji,Rudzinski, Diandra M.,Samankumara, Lalith P.,Ma, Shengli,Grinberg, Nelu,Roschangar, Frank,Yee, Nathan K.,Wang, Guijun,Song, Jinhua J.,Senanayake, Chris H.
supporting information, p. 5474 - 5477 (2015/04/27)
The use of chiral phosphinamides is relatively unexplored because of the lack of a general method for the synthesis. Reported herein is the development of a general, efficient, and highly enantioselective method for the synthesis of structurally diverse P-stereogenic phosphinamides. The method relies on nucleophilic substitution of a chiral phosphinate derived from the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide. These chiral phosphinamides were utilized for the first synthesis of readily tunable P-stereogenic Lewis base organocatalysts, which were used successfully for highly enantioselective catalysis.
Iridium(III)-Catalyzed C H Amidation of Arylphosphoryls Leading to a P-Stereogenic Center
Gwon, Donghyeon,Lee, Donggun,Kim, Jiyu,Park, Sehoon,Chang, Sukbok
supporting information, p. 12421 - 12425 (2016/08/25)
Direct C H amidation of arylphosphoryl compounds has been developed by using an IrIIIcatalyst system under mild conditions. A wide range of substrates could be employed with high functional-group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P-chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de).
Geometrical photoisomerization of (Z)-cyclooctene sensitized by aromatic phosphate, phosphonate, phosphinate, phosphine oxide and chiral phosphoryl esters
Shi, Min,Inoue, Yoshihisa
, p. 2421 - 2427 (2007/10/03)
Aromatic phosphate, phosphonate, phosphinate and phosphine oxide have been used as effective sensitizers for the geometrical photoisomerization of (Z)-cyclooctene (1Z) to its highly strained (E)-isomer (1E). Photosensitizations with phosphate and phosphonate gave moderate photostationary-state E/Z ratios of 0.14-0.17. A comparative study of the fluorescence quenching experiments and kinetic analysis of the product yield demonstrate that the photosensitized isomerization proceeds through a mixed mechanism that involves both singlet and triplet excited states. Triphenylphosphine oxide is not fluorescent and gave a low photostationary-state E/Z ratio of 0.05. Using (-)-menthyl or (-)-bornyl phosphate, phosphonate and phosphinate as chiral sensitizers, the enantiodifferentiating photoisomerization of 1Z was performed to afford optically active 1E in enantiomeric excesses ≤5%.
