42329-48-6Relevant articles and documents
Pd-Catalysed Suzuki coupling of α-bromoethenylphosphonates with organotrifluoroborates: A general protocol for the synthesis of terminal α-substituted vinylphosphonates
Zhang, Li,Fang, Yewen,Jin, Xiaoping,Xu, Housan,Li, Ruifeng,Wu, Hao,Chen, Bin,Zhu, Yiming,Yang, Yi,Tian, Zongming
supporting information, p. 8985 - 8989 (2017/11/09)
A general and robust protocol for the synthesis of terminal α-substituted vinylphosphonates via Suzuki coupling of α-bromovinylphosphonates with organotrifluoroborates has been successfully developed. This method features a broad substrate scope, great functional group compatibilities, and easy scale-up ability. In addition to easy access of nucleophiles, a straightforward synthesis of electrophiles was also realized with diethyl α-bromoethenylphosphonate as the starting material. With a combination of Pd2(dba)3/SPhos as the catalyst, a range of α-alkyl, aryl, heteroaryl, and alkynyl substituted ethenylphosphonates could be nicely accessed under mild conditions. As a synthetic application, the terminal vinylphosphonate was utilized as an effective Michael acceptor in the visible-light-promoted Giese reaction.
α-Phosphonovinyl Arylsulfonates: An Attractive Partner for the Synthesis of α-Substituted Vinylphosphonates through Palladium-Catalyzed Suzuki Reactions
Fang, Yewen,Zhang, Li,Jin, Xiaoping,Li, Jinjian,Yuan, Meijuan,Li, Ruifeng,Wang, Tong,Wang, Tao,Hu, Hanjun,Gu, Juejun
, p. 1577 - 1587 (2016/04/05)
It has been demonstrated that a variety of α-phosphonovinyl arylsulfonates with electron-neutral, -donating, and -withdrawing groups on the phenyl ring could be conveniently and efficiently prepared. In the presence of a Pd(OAc)2/SPhos-based catalyst, various organoboron compounds could be employed as the nucleophilic coupling partners, such as organoboronic acids, boronate esters, and organotrifluoroborates. The newly developed O-centered electrophiles could couple with a multitude of aryl, heteroaryl, and alkylboron reagents, to give α-substituted vinylphosphonates in moderate to excellent yields. Generally, the Suzuki reaction is tolerant of extensive substitution at the aromatic ring of both electrophilic and nucleophilic coupling partners. As in the case of the Suzuki reaction of 8-quinolineboronic acid, proper choice of α-phosphonovinyl arylsulfonates is critical to efficient coupling. Moreover, the prospect for application of this method to complex synthesis has been demonstrated through the coupling of estrone-derived arylborons. The present protocol also features mild conditions and high efficiency. A new and attractive coupling partner for the synthesis of α-substituted vinylphosphonates through Suzuki reactions has been developed. The developed O-centered electrophiles couple with various organoboron reagents to give α-substituted vinylphosphonates in moderate to excellent yields. This protocol features broad substrate scope, mild conditions, and high efficiency.
A simple and efficient method for one-pot, three-component synthesis of terminal vinylphosphonates using a task-specific ionic liquid
Sobhani, Sara,Honarmand, Moones
supporting information, p. 236 - 240 (2013/03/13)
A convenient and practical method for the one-pot, three-component synthesis of terminal vinylphosphonates from readily available starting materials (aryl/alkyl/heteroaryl aldehydes, nitromethane and trialkylphosphites) through a tandem Henry-Michael reaction followed by nitro elimination in the presence of 5-hydroxypentylammonium acetate (5-HPAA) as a task-specific ionic liquid, is described. This method offers several advantages such as the use of a reusable and inexpensive ionic liquid, which is an environmentally benign reaction medium, and a simple reaction setup that does not require specialized equipment. The approach offers good yields of the products under mild reaction conditions. Georg Thieme Verlag Stuttgart New York.
Synthesis of branched 9-[2-(2-phosphonoethoxy)ethyl]purines as a new class of acyclic nucleoside phosphonates which inhibit Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase
Hockova, Dana,Holy, Antonin,Masojidkova, Milena,Keough, Dianne T.,Jersey, John de,Guddat, Luke W.
scheme or table, p. 6218 - 6232 (2011/02/26)
The malarial parasite Plasmodium falciparum (Pf) lacks the de novo pathway and relies on the salvage enzyme, hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT), for the synthesis of the 6-oxopurine nucleoside monophosphates. Specific acyclic
One-pot asymmetric conjugate addition-trapping of zinc enolates by activated electrophiles
Rathgeb, Xavier,March, Sebastien,Alexakis, Alexandre
, p. 5737 - 5742 (2007/10/03)
The copper-catalyzed asymmetric conjugate addition of dialkyl zinc leads to homochiral zinc enolates. These intermediates were trapped in situ with activated allylic electrophiles, without the need of additional palladium catalysis. High trans selectivity
New Synthesis and Hydroboration of Vinylphosphonates
Yamashita, Mitsuji,Kojima, Mitsumasa,Yoshida, Hiroshi,Ogata, Tsuyoshi,Inokawa, Saburo
, p. 1625 - 1628 (2007/10/02)
The Arbuzov reaction of trimethyl and triethyl phosphites with acyl chlorides gave 1-oxoalkylphosphonates in 57-80percent yields.The Wittig reaction of the phosphonates with methylenetriphenylphosphorane gave vinylphosphonates in 25-59percent yields.Hydroboration of vinylphosphonates in oxolane gave 2-hydroxyethylphosphonates in 50-65percent yields.The procedure seems to be a good synthetic method to afford 1-alkyl-substituted 2-hydroxyethylphosphonates which have one more carbon atom than the starting 1-oxoalkylphosphonates.
