25362-01-0Relevant articles and documents
cis-vinylphosphonates and 1,3-butadienylphosphonates by zirconation of 1-alkynylphosphonates
Quntar, Abed Al Aziz,Srebnik, Morris
, p. 1379 - 1381 (2001)
(equation presented) Addition of "zirconocene" to 1-alkynylphosphonates gives three-membered zirconacylces that can be hydrolyzed to cis-vinylphosphonates or further reacted with alkynes/hydrolysis to give substituted (Z,E)- and (E,E)-1,3-butadienylphosph
Regio- and stereospecific hydrophosphorylation of phenylacetylene
Kuramshin, Arcady I.,Nikolaev, Andrey A.,Cherkasov, Rafael A.
, p. 155 - 156 (2005)
The interaction of diethyl phosphite with phenylacetylene within the coordination sphere of the trialkynemonocarbonyl-molybdenum(0) complex produces diethyl (Z)-2-phenylvinylphosphonate.
Inverting External Asymmetric Induction via Selective Energy Transfer Catalysis: A Strategy to β-Chiral Phosphonate Antipodes
Onneken, Carina,Bussmann, Kathrin,Gilmour, Ryan
, p. 330 - 334 (2019/12/11)
Enantiodivergent, catalytic reduction of activated alkenes relays stereochemical information encoded in the antipodal chiral catalysts to the pro-chiral substrate. Although powerful, the strategy remains vulnerable to costs and availability of sourcing bo
Suzuki and Stille Cross-Coupling Reactions from β-Iodovinylphosphonate: Stereoselective Access to Various Substituted Vinylphosphonates
Thiery, Emilie,Abarbri, Mohamed
, p. 2757 - 2762 (2015/02/19)
Stereoselective synthesis of β-arylvinyl, dienyl, and enynylphosphonates was achieved from diethyl 2-iodovinylphosphonate via Suzuki or Stille cross-coupling reactions in good yields.
Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides
Liu, Liu,Wang, Yulei,Zeng, Zhiping,Xu, Pengxiang,Gao, Yuxing,Yin, Yingwu,Zhao, Yufen
supporting information, p. 659 - 666 (2013/04/10)
A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright
CuSO4/Al2O3 as a new effective and recyclable catalyst for the arylation of dialkyl phosphites
Karlstedt,Anokhin,Beletskaya
, p. 2498 - 2499 (2014/11/08)
A new effective recycled catalyst CuSO4/Al2O 3, which performs the phosphorylation of aryl halides and bromostyrene, was proposed.
Key structural features of cis-cinnamic acid as an allelochemical
Abe, Masato,Nishikawa, Keisuke,Okuda, Katsuhiro,Shindo, Mitsuru,Fukuda, Hiroshi,Nakanishi, Kazunari,Tazawa, Yuta,Taniguchi, Tomoya,Park, So-Young,Hiradate, Syuntaro,Fujii, Yoshiharu
, p. 56 - 67,12 (2012/12/12)
1-O-cis-cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the cis-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclohexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated.
Copper-mediated selective cross-coupling of 1,1-dibromo-1-alkenes and heteronucleophiles: Development of general routes to heterosubstituted alkynes and alkenes
Jouvin, Kevin,Coste, Alexis,Bayle, Alexandre,Legrand, Frederic,Karthikeyan, Ganesan,Tadiparthi, Krishnaji,Evano, Gwilherm
, p. 7933 - 7947 (2013/01/16)
Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing
Copper-mediated cross-coupling of 1,1-dibromo-1-alkenes with dialkyl phosphites: A convenient synthesis of 1-alkenylphosphonates
Evano, Gwilherm,Tadiparthi, Krishnaji,Couty, Francois
supporting information; experimental part, p. 179 - 181 (2011/02/25)
An efficient and stereoselective procedure for the preparation of E-1-alkenylphosphonates by copper-mediated cross-coupling between 1,1-dibromo-1-alkenes and dialkyl phosphites is reported. The reaction allows for formal substitution of both bromine atoms
Reaction of diethyl thiocyanatomethylphosphonate with aldehydes as a route to diethyl Z-1-alkenylphosphonates
Blaszczyk, Roman,Gajda, Tadeusz
, p. 732 - 739 (2008/03/18)
Diastereoselective synthesis of diethyl Z-1-alkenylphosphonates from easily available diethyl thiocyanatomethylphosphonate and aromatic aldehydes has been developed. Olefination of the aldehydes occurs under mild conditions and affords the title compounds with moderate yields. A plausible mechanism of the above-mentioned reaction is also discussed.
