884-90-2Relevant articles and documents
Toward the Efficient Synthesis of New Phosphopantothenate Derivatives by Using Chlorophosphate Reagents
Pahor, Jerca,Stavber, Stojan,?usak, Alen,Kosec, Gregor,Petkovi?, Hrvoje,Berke, Ajda Podgor?ek
, p. 3763 - 3772 (2016)
Seven new masked analogues of phosphopantothenate, suitable for an evaluation of their potential ability to restore intracellular coenzyme A (CoA) levels, were successfully synthesized in good to moderate yields. The preparation of derivatives masked with (acyloxy)alkyl groups was studied particularly in terms of synthetic efficiency, and the possibility of applying different chlorophosphate reagents for the preparation of a variety of masked derivatives was also investigated. Using this methodology, we have successfully synthesized a new chlorophosphate reagent, suitable for the introduction of the (isobutyryloxy)methyl functionality into the prodrug. Additionally, special attention was given to finding mild and economical reaction conditions for phosphorylation of biological molecules.
Palladium/Xiao-Phos-Catalyzed Kinetic Resolution of sec-Phosphine Oxides by P-Benzylation
Dai, Qiang,Liu, Lu,Zhang, Junliang
supporting information, p. 27247 - 27252 (2021/11/17)
P-stereogenic tert- and sec-phosphines have wide applications in asymmetric catalysis, materials, and pharmaceutical chemistry, however, their practical synthesis still constitutes a significant challenge. Herein, a successful kinetic resolution of rac-se
Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates
Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, p. 5342 - 5347 (2021/06/30)
A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.
O-Phosphination of Aldehydes/Ketones toward Phosphoric Esters: Experimental and Mechanistic Studies
Qian, Yanyan,Dai, Qiang,Li, Zhiming,Liu, Yu,Zhang, Junliang
supporting information, p. 4742 - 4748 (2020/06/29)
Addition of P-H species to carbonyl groups, namely the Pudovik reaction, normally delivers hydroxyl phosphorus compounds, along with phosphate byproducts in some cases. A few controllable systems starting from phosphites were set up to mainly provide the phosphates. Herein, we present a highly selective protocol starting from phosphonate precursors leading to phosphinate derivatives. Enantioenriched phosphinates were successfully achieved from chiral phosphine oxide precursors. Experimental and theoretical investigations were conducted to understand the mechanistic details.
Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3-Catalyzed Friedel–Crafts-Type Benzylation
Yurino, Taiga,Hachiya, Asuka,Suzuki, Keisuke,Ohkuma, Takeshi
, p. 2225 - 2232 (2020/04/16)
Al(OTf)3 was identified as a high-performance catalyst for Friedel–Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.
Cetyltrimethyl ammonium bromide catalysed oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds
Li, Hang,Lei, Jian,Liu, Yongping,Chen, Yi,Au, Chak-Tong,Yin, Shuang-Feng
, p. 302 - 308 (2019/01/10)
An efficient metal-free method for the synthesis of organophosphorus compounds via oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds catalysed by cetyltrimethyl ammonium bromide (CTAB) is
BuLi-triggered phospha-Brook rearrangement: Efficient synthesis of organophosphates from ketones and aldehydes
Pallikonda, Gangaram,Santosh, Ranga,Ghosal, Subhas,Chakravarty, Manab
, p. 3796 - 3798 (2015/06/08)
A variety of organophosphates are synthesized from n-BuLi-triggered, (additional) solvent-free reactions of diethyl phosphite with both activated/unactivated ketones and aldehydes preferably at room temperature via phospha-Brook rearrangement. We could successfully synthesize the naphthylic/allylic phosphates using this approach.
Tetrabutylammonium iodide-catalyzed phosphorylation of benzyl c-h bonds via a cross-dehydrogenative coupling (cdc) reaction
Xu, Jian,Zhang, Pengbo,Li, Xueqin,Gao, Yuzhen,Wu, Ju,Tang, Guo,Zhaoa, Yufen
, p. 3331 - 3335 (2015/01/16)
Phosphate esters play important roles as biological active principles and synthons in chemistry. An efficient metal-free approach for the synthesis of phosphate esters through sp3 C-H activation is described. By using tetrabutylammonium iodide (Bu4NI) as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant, various toluene derivatives and phosphorus nucleophiles are tolerated in this transformation, affording the corresponding products in moderate to good yields.
Synthesis of diarylmethanes through palladium-catalyzed coupling of benzylic phosphates with arylsilanes
Zhang, Pengbo,Xu, Jian,Gao, Yuzhen,Li, Xueqin,Tang, Guo,Zhao, Yufen
, p. 2928 - 2932 (2015/01/16)
An efficient approach to the benzylation of arenes has been developed. The reactions described provide straightforward access to diarylmethanes through Pd-catalyzed coupling of benzylic phosphates with arylsilanes in good to excellent yields. The reaction tolerates a wide range of functionalities such as halide, alkoxyl, and nitro groups.
