2021
DOI: 10.1039/d0gc04395h
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A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones

Abstract: The unique reactivity profile of -chloronitroso derivatives is expressed to its fullest potential through the development of an integrated, modular and scalable continuous flow process for the electrophilic α-aminohydroxylation of...

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Cited by 21 publications
(19 citation statements)
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“…Full concatenation of a similar process was demonstrated elsewhere. 70 With a 60 s residence time at 0 °C, the oxidation of CEES reached 99% conversion with a 96% selectivity toward CEESO . The major impurity became mono-chlorinated sulfoxide CEESOCl , while sulfone CEESO 2 remained undetected, hence providing a neutralization selectivity of 99% with a space time yield = 3.74 kg L −1 h −1 .…”
Section: Resultsmentioning
confidence: 97%
“…Full concatenation of a similar process was demonstrated elsewhere. 70 With a 60 s residence time at 0 °C, the oxidation of CEES reached 99% conversion with a 96% selectivity toward CEESO . The major impurity became mono-chlorinated sulfoxide CEESOCl , while sulfone CEESO 2 remained undetected, hence providing a neutralization selectivity of 99% with a space time yield = 3.74 kg L −1 h −1 .…”
Section: Resultsmentioning
confidence: 97%
“…[15] The Efactor value is inherently related to the nature and the context of process: (a) oil refining is usually associated with a very low E-factor (< 1); (b) production roads leading to bulk chemical are usually characterized with E-factors ranging from 1 to 5; (c) processes toward fine chemicals procedures have E-factors in the 5-50 range and (d) the production of pharmaceuticals should not exceed an E-factor of 100. [234,235] These numbers are correlated with the complexity and the number of steps. As the upgraded molecules discussed in this work have predominant applications at the interface between bulk chemicals and fine chemicals, processes with E-factors ranging from 1 to 50 would be acceptable.…”
Section: Homogeneous Acidic Catalystsmentioning
confidence: 99%
“…It is defined as the ratio of the total mass of waste on the mass of synthesized product while lower value is interpreted as a process with a global low environmental footprint [15] . The E‐factor value is inherently related to the nature and the context of process: (a) oil refining is usually associated with a very low E‐factor (<1); (b) production roads leading to bulk chemical are usually characterized with E‐factors ranging from 1 to 5; (c) processes toward fine chemicals procedures have E‐factors in the 5–50 range and (d) the production of pharmaceuticals should not exceed an E‐factor of 100 [234,235] . These numbers are correlated with the complexity and the number of steps.…”
Section: Staple Reactions Toward the Upgrading Of Bio‐based Vicinal P...mentioning
confidence: 99%
“…1A and Table 1). Building upon our previous work on developing more rational, sustainable, and low environmental footprint flow processes for accessing high value-added active pharmaceutical ingredients, [36][37][38] a solution was sought for the continuous manufacturing of modafinil (1). The approach presented herein is not restricted to a simple transposition of existing batch protocols under continuous flow conditions, but rather it encompasses a holistic approach with a careful selection and re-optimization of upstream process conditions to ease downstream purification and hence ensure overall low environmental footprint for accessing modafinil.…”
Section: Introductionmentioning
confidence: 99%