CDI-promoted direct esterification of P(O)-OH compounds with phenols

Xiong, Biquan; Hu, Chenghong; Li, Haotian; Zhou, Congshan; Zhang, Pangliang; Liu, Yu; Tang, Kewen

doi:10.1016/j.tetlet.2017.05.036

Cited by 23 publications

(19 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…44 31 P NMR (CDCl 3 ):  = 1.1 ppm; m/z 141 [M + H] + H 3 PO 4 : 31 P NMR (DMSO-d 6 ):  = -0.06 ppm. 31 P NMR (CDCl 3 ):  = 0 ppm}. This kind of dealkylation was observed by us during alcoholyses.…”

Section: Paper Synthesis Table 1 Direct Esterification Of Monobutylph...mentioning

confidence: 57%

“…29 The esterification of P-acids, especially that of phosphinic acids, is a hot topic. Xiong and Tang together with co-workers elaborated the esterification of phosphinic acids applying coupling agents, such as N,N′-carbonyl diimidazole 30,31 or uronium-based salts, 30,32 or using cyclic diaryliodonium salts as the reactant, leading to diphenylation. 33 Our group has experience in the microwave (MW)-assisted direct esterification of P-acids.…”

Section: Paper Synthesismentioning

confidence: 99%

“…a On the basis of the relative31 P NMR integrals found in the spectrum of the crude mixture. b No change on further irradiation.…”

mentioning

confidence: 99%

See 2 more Smart Citations

P-Chloride-Free Synthesis of Phosphoric Esters: Microwave-Assisted Esterification of Alkyl- and Dialkyl Phosphoric Ester-Acids Obtained from Phosphorus Pentoxide

Harsági¹,

Kiss²,

Keglevich³

2022

Synthesis

View full text Add to dashboard Cite

It is a reasonable endeavour to replace P-chloride starting materials (e.g. POCl3) by greener and cheaper reagents. Our purpose was to start from phosphorus pentoxide, i.e. to utilize its reaction with alcohols in the preparation of (HO)2P(O)(OR) and HOP(O)(OR)2, and to convert the mixtures of the corresponding monoester and diester so obtained to the target trialkyl esters. Separate experiments showed that the monobutylphosphate undergo microwave (MW)-assisted esterification with butanol in the presence of [bmim][BF4] catalyst at 200 °C to afford dibutylphosphate in a selective manner (~95%) that, in turn, may be converted to tributylphosphate by alkylation under MW irradiation. In this way, the mixtures of (HO)2P(O)(OR) and HOP(O)(OR)2 obtained by the practical reaction of phosphorus pentoxide and alcohol (ROH) could also be converted in two additional steps to the corresponding trialkyl esters. The three-step synthesis of trialkylphosphates starting from phosphorus pentoxide was also transformed in a one-pot (step 1: preparation of the monoester diester mixture, step 2: diesterification) and telescoping (step 3: triesterification) variation avoiding the isolation and purification of the intermediates, and affording the triesters in 86-93% yields. The three- and two-step P-chloride-free methods developed are “green” and of more general value.

show abstract

Section: Paper Synthesis Table 1 Direct Esterification Of Monobutylph...mentioning

confidence: 57%

Section: Paper Synthesismentioning

confidence: 99%

See 1 more Smart Citation

P-Chloride-Free Synthesis of Phosphoric Esters: Microwave-Assisted Esterification of Alkyl- and Dialkyl Phosphoric Ester-Acids Obtained from Phosphorus Pentoxide

Harsági¹,

Kiss²,

Keglevich³

2022

Synthesis

View full text Add to dashboard Cite

show abstract

“…also elaborated efficient esterifications of phosphinic acids with alcohols. They applied copper catalyst or activating agents [25][26][27].…”

Section: Possible Syntheses Of Phosphinates With Stress On the Mw-assmentioning

confidence: 99%

<strong>The potential and scope of the microwave tool; A case study on the synthesis of phosphinates </strong>

Keglevich

Kiss

2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

Microwave (MW) irradiation has had a positive impact also on organophosphorus chemistry. This is demonstrated via the synthesis of phosphinates from phosphinic acids. The scope and limitations of the use of the MW technique, along with the modeling of the distribution of the beneficial effect of the local overheatings and the prediction of the acceleration is discussed. All these are possible on the basis of the energetics calculated for a selected esterification by quantum chemical methods.Keywords: phosphinic acid; phosphinate; microwave; ionic liquid; green chemistry; scope and limitation of the use of MW; modeling the effect of MW; conformation

show abstract

“…Dhawan 等 [23] 在 2010 年, 陈建添等 [28] 备磷酸混酯的研究中发现, 氯化硅(SiO 2 -Cl) (Scheme 14) [32] 和对甲苯磺酸-硅藻土复合材料(p-TsOH-Celite) [33] 均表现出较高的非均相催化活性, 特别是后者, 两种反应底物磷酸二苯酯和乙醇的物质的量比仅为 1∶1, 反应可以顺利进行(Scheme 15), 上述两种方法操作简单、条件温和且转化效率高, 在室温～40 ℃条件下反应 10～40 min, 即可高效得到目标产物, 分离产率高达 96%. 近年来, 熊碧泉和唐课文课题组先后报道了将 Cu 催化的 Chan-Lam 类型的偶联反应 [37] 、N,N'-羰基二咪唑 (CDI) [38] 、脲阳离子盐 [39] 以及 N,N'-二环己基碳二亚胺 (DCC) [40] 催化的酯化反应, 应用于芳基、烷基磷酸混酯的制备中, 然而, 反应活性较低, 结果也不尽如人意. [42] .…”

unclassified

Research Progress in the Preparation of Aryl and Alkyl Mixed Phosphates

Jiao¹,

Yu²,

Ning³

et al. 2021

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

Aryl and alkyl mixed phosphates are very important phosphorus containing organic compounds, which are widely used in many fields, such as biology, medicine, pesticide, polymer, and material science. The unique physical, chemical, and biological properties of phosphorus-based motifs provide more possibilities for their structural modification, derivatization, and potential application. Therefore, the research on the preparation of these compounds has important theoretical and practical significance. In this paper, the research progress of the synthesis methodologies of aryl and alkyl mixed phosphate in the past few decades is reviewed. The application examples are listed. The experimental methods and development process of the conversion of various kinds of phosphorus containing reagents to target compounds are summarized. The characteristics, mechanism, and application of the reaction are discussed selectively as well. We hope that this review can provide a reference for the development of new preparation protocols of mixed phosphate, and provide some useful references for scholars, graduate students, and others in the related fields.

show abstract

CDI-promoted direct esterification of P(O)-OH compounds with phenols

Cited by 23 publications

References 41 publications

P-Chloride-Free Synthesis of Phosphoric Esters: Microwave-Assisted Esterification of Alkyl- and Dialkyl Phosphoric Ester-Acids Obtained from Phosphorus Pentoxide

P-Chloride-Free Synthesis of Phosphoric Esters: Microwave-Assisted Esterification of Alkyl- and Dialkyl Phosphoric Ester-Acids Obtained from Phosphorus Pentoxide

<strong>The potential and scope of the microwave tool; A case study on the synthesis of phosphinates </strong>

Research Progress in the Preparation of Aryl and Alkyl Mixed Phosphates

Contact Info

Product

Resources

About

CDI-promoted direct esterification of P(O)-OH compounds with phenols

Cited by 23 publications

References 41 publications

P-Chloride-Free Synthesis of Phosphoric Esters: Microwave-Assisted Esterification of Alkyl- and Dialkyl Phosphoric Ester-Acids Obtained from Phosphorus Pentoxide

P-Chloride-Free Synthesis of Phosphoric Esters: Microwave-Assisted Esterification of Alkyl- and Dialkyl Phosphoric Ester-Acids Obtained from Phosphorus Pentoxide

<strong>The potential and scope of the microwave tool; A case study on the synthesis of phosphinates&nbsp;</strong>

Research Progress in the Preparation of Aryl and Alkyl Mixed Phosphates

Contact Info

Product

Resources

About

<strong>The potential and scope of the microwave tool; A case study on the synthesis of phosphinates </strong>