Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions

Justin D. Smith; Tharique N. Ansari; Martin P. Andersson; Dongari Yadagiri; Faisal Ibrahim; Shengzong Liang; Gerald B. Hammond; Fabrice Gallou; Sachin Handa

doi:10.1039/c7gc03514d

Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions

Justin D. Smith
, Tharique N. Ansari
, Martin P. Andersson
, Dongari Yadagiri
, Faisal Ibrahim
, Shengzong Liang
, Gerald B. Hammond
, Fabrice Gallou
, Sachin Handa^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

76 Scopus citations

Abstract

Proline-based designer surfactant FI-750-M has been demonstrated to enable selective nucleophilic aromatic substitution of polyfluoro(hetero)arenes by sulfinate salts in water under mild micellar conditions. Resultant sulfones were obtained from diverse substrates in good yields without side product formation and could usually be purified by simple filtration. The nature of micelles of FI-750-M and the solubility of coupling partners in different micellar regions has been supported by dynamic light scattering, cryo-TEM, and DFT calculations.

Original language	English
Pages (from-to)	1784-1790
Number of pages	7
Journal	Green Chemistry
Volume	20
Issue number	8
DOIs	https://doi.org/10.1039/c7gc03514d
State	Published - 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

ASJC Scopus subject areas

Environmental Chemistry
Pollution

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10.1039/c7gc03514d

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title = "Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions",

abstract = "Proline-based designer surfactant FI-750-M has been demonstrated to enable selective nucleophilic aromatic substitution of polyfluoro(hetero)arenes by sulfinate salts in water under mild micellar conditions. Resultant sulfones were obtained from diverse substrates in good yields without side product formation and could usually be purified by simple filtration. The nature of micelles of FI-750-M and the solubility of coupling partners in different micellar regions has been supported by dynamic light scattering, cryo-TEM, and DFT calculations.",

author = "Smith, \{Justin D.\} and Ansari, \{Tharique N.\} and Andersson, \{Martin P.\} and Dongari Yadagiri and Faisal Ibrahim and Shengzong Liang and Hammond, \{Gerald B.\} and Fabrice Gallou and Sachin Handa",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c7gc03514d",

language = "English",

volume = "20",

pages = "1784--1790",

journal = "Green Chemistry",

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T1 - Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions

AU - Smith, Justin D.

AU - Ansari, Tharique N.

AU - Andersson, Martin P.

AU - Yadagiri, Dongari

AU - Ibrahim, Faisal

AU - Liang, Shengzong

AU - Hammond, Gerald B.

AU - Gallou, Fabrice

AU - Handa, Sachin

PY - 2018

Y1 - 2018

N2 - Proline-based designer surfactant FI-750-M has been demonstrated to enable selective nucleophilic aromatic substitution of polyfluoro(hetero)arenes by sulfinate salts in water under mild micellar conditions. Resultant sulfones were obtained from diverse substrates in good yields without side product formation and could usually be purified by simple filtration. The nature of micelles of FI-750-M and the solubility of coupling partners in different micellar regions has been supported by dynamic light scattering, cryo-TEM, and DFT calculations.

AB - Proline-based designer surfactant FI-750-M has been demonstrated to enable selective nucleophilic aromatic substitution of polyfluoro(hetero)arenes by sulfinate salts in water under mild micellar conditions. Resultant sulfones were obtained from diverse substrates in good yields without side product formation and could usually be purified by simple filtration. The nature of micelles of FI-750-M and the solubility of coupling partners in different micellar regions has been supported by dynamic light scattering, cryo-TEM, and DFT calculations.

UR - https://www.scopus.com/pages/publications/85045873473

U2 - 10.1039/c7gc03514d

DO - 10.1039/c7gc03514d

M3 - Article

AN - SCOPUS:85045873473

SN - 1463-9262

VL - 20

SP - 1784

EP - 1790

JO - Green Chemistry

JF - Green Chemistry

IS - 8

ER -

Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions

Abstract

Bibliographical note

ASJC Scopus subject areas

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