912-28-7Relevant academic research and scientific papers
Potassium carbonate promoted nucleophilic addition of alkenes with phosphites
Huang, Zhenjun,Liu, Wei,Li, Sen,Yang, Yutian,Guo, Shengmei,Cai, Hu
supporting information, p. 1295 - 1297 (2020/08/21)
A facile hydrophosphonylation of alkenes by phosphites promoted by potassium carbonate was developed. The reaction features include easy handling, environmental friendliness, and avoidance of the use of strong bases. A variety of alkenes are tolerated in this reaction, with moderate to excellent yields.
Zn(OTf)2-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides
Shan, Changkai,Chen, Fushan,Pan, Jiaoting,Gao, Yuxing,Xu, Pengxiang,Zhao, Yufen
supporting information, p. 11659 - 11666 (2017/11/10)
The first facile and efficient Zn(OTf)2-catalyzed direct coupling of unprotected propargylic alcohols with arylphosphine oxides has been developed, affording a general, one-step approach to access structurally diverse γ-ketophosphine oxides via sequential Meyer-Schuster rearrangement/phospha-Michael reaction along with new C(sp3) - P and C=O bond formations, operational simplicity, and complete atom economy under ligand-free and base-free conditions.
Synthesis of new phosphonoamide and phosphonocaprolactam derivatives via the diethyl chlorophosphate-promoted beckmann rearrangement of γ-phosphonyloximes
Wahbi, Aymen,Touil, Soufiane
, p. 397 - 404 (2017/02/14)
ABSTRACT: Herein, we report an efficient and straightforward synthesis of new phosphonoamide and phosphonocaprolactam derivatives, via the Beckmann rearrangement of γ-phosphonyloximes. The reaction proceeded smoothly in the presence of diethyl chlorophosp
Versatile syntheses of optically pure pce pincer ligands: Facile modifications of the pendant arms and ligand backbones
Yang, Xiang-Yuan,Tay, Wee Shan,Li, Yongxin,Pullarkat, Sumod A.,Leung, Pak-Hing
supporting information, p. 1582 - 1588 (2015/05/13)
A series of chiral C-stereogenic PCP and PCN ligand precursors were prepared in situ from inexpensive achiral starting materials via a simple catalytic asymmetric P-H addition reaction in good overall yields. This facile catalytic method of preparing the ligand backbones renders easy and economical modifications of the electronically crucial para-substituent, chiral functionalities, and donor atoms for different transition metal ions. A one-pot synthetic procedure was used efficiently to prepare the corresponding optically pure pincer complexes. All the new complexes were characterized by NMR and mass spectroscopy. The molecular structures of several selected complexes have also been elucidated by X-ray crystallography. Preliminary studies indicated that minor structural changes on these novel pincer complexes affect their chemical properties significantly when they were applied as catalysts for the reaction between diphenylphosphine and chalcone.
N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts
Hans, Morgan,Delaude, Lionel,Rodriguez, Jean,Coquerel, Yoann
, p. 2758 - 2764 (2014/04/17)
N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC·CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.
Phospha-Michael additions to activated internal alkenes: Steric and electronic effects
Lenker, Heather K.,Richard, Marcia E.,Reese, Kyle P.,Carter, Anthony F.,Zawisky, Jason D.,Winter, Eric F.,Bergeron, Timothy W.,Guydon, Krysta S.,Stockland, Robert A.
experimental part, p. 1378 - 1385 (2012/03/11)
The addition of P(O)-H bonds to internal alkenes has been accomplished under solvent-free conditions without the addition of a catalyst or radical initiator. Using a prototypical secondary phosphine oxide, a range of substrates including cinnamates, crotonates, coumarins, sulfones, and chalcones were successfully functionalized. Highly activated acceptors such as isopropylidenemalononitrile and ethyl 2-cyano-3-methyl-2-butenoate underwent the phospha-Michael reaction upon simple trituration of the reagents at room temperature, whereas less activated substrates such as ethyl cinnamate and methyl crotonate required heating (>150 °C) in a microwave reactor to achieve significant consumption of the starting alkenes. For the latter alkenes, a competing reaction involving disproportionation of the ditolylphosphine oxide into ditolylphosphinic acid and ditolylphosphine was observed at the high temperatures needed to promote the addition reaction.
Unsymmetrical chiral PCN pincer palladium(II) and nickel(II) complexes with aryl-based aminophosphine-imidazoline ligands: Synthesis via aryl C-H activation and asymmetric addition of diarylphosphines to enones
Yang, Ming-Jun,Liu, Yan-Jing,Gong, Jun-Fang,Song, Mao-Ping
experimental part, p. 3793 - 3803 (2011/09/20)
Figure Persented: Chiral 3-(2′-imidazolinyl)anilines 3a-c were easily synthesized by converting the carboxyl and nitro groups in commercially available 3-nitrobenzoic acid to chiral imidazoline and amine, respectively. The one-pot phosphorylation/metalati
Asymmetric organocatalytic conjugate addition of diarylphosphane oxides to chalcones
Russo, Alessio,Lattanzi, Alessandra
supporting information; experimental part, p. 6736 - 6739 (2011/02/28)
The first example of a convenient and enantioselective asymmetric conjugate addition of diarylphosphane oxides to chalcones is reported. By using commercially available dihydroquinine as the organocatalyst and diphenylphosphane oxide as the nucleophile, t
Palladium(II)-catalyzed conjugate phosphination of electron-deficient acceptors
Trepohl, Verena T.,Mori, Susumu,Itami, Kenichiro,Oestreich, Martin
supporting information; experimental part, p. 1091 - 1094 (2009/07/25)
A general protocol for the conjugate transfer of diphenyl-, dicyclohexyl-, and di-tert-butylphosphinyl groups from silylphosphines to cyclic and acyclic electron-deficient acceptors employing a bench-stable palladium(II) catalyst is reported. Several Eand
