An efficient and general route to the synthesis of diethyl α,α-bromofluorophosphonates

Fu, Jianping; He, Yan‐Hong; Zhong, Jun; Yang, Yang; Deng, Xiang; Guan, Zhi

doi:10.1016/j.jfluchem.2011.06.016

Cited by 7 publications

(9 citation statements)

References 16 publications

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“…A further variation involves the use of tetrabutylammonium bromide as the nucleophile in the presence of triphenylphosphine—DDQ (2,3-dichloro-5,6-dicyanobenzoquinone) system, affording α-bromophosphonates [ 115 , 116 ].…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

“…As a variation of this method, a protocol applying morpholinosulfur trifluoride was elaborated for the OH → F change in α-hydroxy-bisphosphonates [ 122 ]. N -fluorobisbenzenesulfonimide was used efficiently to introduce a fluoro function to the α-carbon atom of α-monohalophosphonates 38 in the presence of sodium hexamethyldisilazane [ 113 , 114 , 116 ].…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

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Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids.

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Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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“…57 Mechanistic studies appear to rule out a radical pathway. Scheme 8 shows an example using an alkyl phosphonate.…”

Section: Aliphatic A-bromophosphonatesmentioning

confidence: 99%

“…Scheme 8 shows an example using an alkyl phosphonate. 57 We focus now on examples of aliphatic a-bromophosphonates that have been assayed as inhibitors of phosphate recognizing proteins. 57 Mechanistic studies appear to rule out a radical pathway.…”

Section: Aliphatic A-bromophosphonatesmentioning

confidence: 99%

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Synthesis of α-brominated phosphonates and their application as phosphate bioisosteres

Downey

Cairo

2014

Med. Chem. Commun.

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Substrate phosphorylation is a key modulator of signal transduction. Abnormal phosphorylation in vivo is implicated in many diseases including cancer, diabetes, and Alzheimer's disease. Inhibitors of phosphaterecognizing proteins have potential as medicinal agents as well as tools to study phosphorylation pathways. A well-known and common inhibition strategy is to synthetically replace the labile phosphate moiety with a non-hydrolyzable phosphonate. Fully saturated, a-fluoro and a,a-difluorophosphonates are often effective phosphate bioisosteres and have been well studied. More recently a-brominated phosphonates have begun to emerge as inhibitors of phosphate recognizing enzymes, some of which operate by irreversible mechanisms. Herein we discuss the synthetic approaches to aliphatic and benzylic a-bromophosphonates and their biological activities.Scheme 5 The synthesis of an aliphatic a-bromophosphonate derivative. 52 Scheme 6 An improved synthetic strategy to alkyl abromophosphonates. 53This journal is

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ChemInform Abstract: An Efficient and General Route to the Synthesis of Diethyl α,α‐Bromofluorophosphonates.

Zhong

et al. 2011

ChemInform

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An efficient and general route to the synthesis of diethyl α,α-bromofluorophosphonates

Cited by 7 publications

References 16 publications

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis of α-brominated phosphonates and their application as phosphate bioisosteres

ChemInform Abstract: An Efficient and General Route to the Synthesis of Diethyl α,α‐Bromofluorophosphonates.

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