TBAI/TBHP mediated oxidative cross coupling of aryl alkyl ketones with H-phosphonates and H-phosphine oxides in water: facile access to ketol phosphates and phosphinates

Saidulu, G.; Kumar, Rakesh; Anitha, T.; Kumar, Pankaj; Reddy, K. Rajender

doi:10.1016/j.tetlet.2016.02.095

Cited by 9 publications

(3 citation statements)

References 52 publications

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“…Scheme depicts our designed reaction, in which, in the presence of Et 3 N and CCl 4 , nitrone reacts with dialkyl H -phosphonates to give intermediate A , followed by in situ hydrolysis to yield the target product α-keto phosphates. Up to this point, only a limited number of synthetic methods toward α-keto phosphates have been reported . In 1988, Koser et al successfully developed a two-step synthetic method toward some α-keto phosphates .…”

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confidence: 99%

A Multiheteroatom [3,3]-Sigmatropic Rearrangement: Disproportionative Entries into 2-(N-Heteroaryl)methyl Phosphates and α-Keto Phosphates

Yang

Chen

et al. 2017

Org. Lett.

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confidence: 99%

A Multiheteroatom [3,3]-Sigmatropic Rearrangement: Disproportionative Entries into 2-(N-Heteroaryl)methyl Phosphates and α-Keto Phosphates

Yang

Chen

et al. 2017

Org. Lett.

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“…Single‐step or one‐pot synthesis for α‐phosphonyloxy ketones is more attractive than two‐step approaches including extra synthetic step of intermediates (Scheme ) . The routes reported in the literature for the synthesis of α‐phosphonyloxy ketones require a long time up to 48 h at room temperature (RT), 4 h to 48 h even at high temperature ( up to 80 °C), and also produce massive by‐products, (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

“…Importantly, using this approach, α‐phosphonyloxy ketones could be easily access at room temperature in fast (residence time 3.93 s), safe, environmentally benign and compact compared to conventional batch process. Moreover, most of the reported methods involves various phosphites as starting materials known as potentially neurotoxic reagents for the synthesis of α‐phosphonyloxy ketones.…”

Section: Methodsmentioning

confidence: 99%

Fast‐Synthesis of α‐Phosphonyloxy Ketones as Drug Scaffolds in a Capillary Microreactor

et al. 2019

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A simple, room temperature approach for the fast single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, has been developed which involves highly reactive species i.e., 1,2-dicarbonyls that readily react with trialkyl phosphites and formic acids in batch as well as in continuous-flow with the flow rate of 3 ml/min (t R = ∼4 s). The present approach reduced the synthesis time from hours to minutes in batch, which was further lowered to a few seconds precisely controlled by single capillary microfluidics. A wide range of 1,2-dicarbonyl deriva-Continuous-flow microreactors have recently attracted much attention as an important technique for synthesizing organic molecules including drug intermediates/molecules in a very short time under mild reaction conditions. [1][2][3][4] A high surface area to volume ratio in this microfluidic system promotes mass and heat transfer, leading to selectivity and conversion much superior to the levels obtainable by conventional batch processes. [2][3][4] Owing to their many complex issues such as inefficient mixing, non-uniformity in heat, and safety in the scale-up of batch process, in recently, flow approach is more attractive and reliable in both academia and industry. [1,2] Furthermore, high throughput production can be achieved by simply increasing reaction volume with larger dimension of channel, or/and by numbering up microreactor units in parallel. [5,6] In light of the push for continuous manufacturing of pharmaceutical products [7,8] microreactor can be an attractive alternative to the conventional batch process for many of the pharmaceutical products whose world-wide consumption is of the order of tons a year. Therefore, simple and fast continuous-flow methodologies are highly desirable to operate at high flow rate, enabling to satisfy the changing needs of pharmaceutical markets in a safe and environmentally benign, cost-effective manner.On the other hand, the organophosphate chemistry by itself is an interesting area of organic chemistry as well as life science in living organism such as DNA, RNA, ATP and cell membranes. [9] Moreover, various methodologies also reported for [a] Dr. 7730Scheme 4. Control experiments in batch to understand the reaction mechanism.Scheme 5. Plausible reaction mechanism for the synthesis of α-phosponyloxy ketone.

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Oxidation and Reduction

Banerji¹

2020

Organic Reaction Mechanisms · 2016

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TBAI/TBHP mediated oxidative cross coupling of aryl alkyl ketones with H-phosphonates and H-phosphine oxides in water: facile access to ketol phosphates and phosphinates

Cited by 9 publications

References 52 publications

A Multiheteroatom [3,3]-Sigmatropic Rearrangement: Disproportionative Entries into 2-(N-Heteroaryl)methyl Phosphates and α-Keto Phosphates

A Multiheteroatom [3,3]-Sigmatropic Rearrangement: Disproportionative Entries into 2-(N-Heteroaryl)methyl Phosphates and α-Keto Phosphates

Fast‐Synthesis of α‐Phosphonyloxy Ketones as Drug Scaffolds in a Capillary Microreactor

Oxidation and Reduction

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