ChemInform Abstract: 1‐Alkyl‐4‐fluoro‐1,4‐diazoniabicyclo(2.2.2)octane Salts: A Novel Family of Electrophilic Fluorinating Agents.

Banks, R. E.; Mohialdin-Khaffaf, Suad N.; Lal, G. S.; Sharif, Iqbal; Syvret, Robert G.

doi:10.1002/chin.199239220

Cited by 2 publications

(2 citation statements)

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“…In the summer of 1997, I enjoyed the 15 th International Symposium on Fluorine Chemistry (Vancouver), where I met Dr. R. G. Syvret. He introduced me with Selectfluor as a new electrophilic fluorinating reagent [6,16] . While preparing CMIT−F with one of my students, Miss E. Suzuki, we found that molecular structure of Selectfluor has similarities with Cinchona alkaloids, which have a laudable history in asymmetric synthesis.…”

Section: The Birth Of An Ideamentioning

confidence: 89%

N‐Fluoro Ammonium Salts of Cinchona Alkaloids in Enantioselective Electrophilic Fluorination

Shibata

Cahard

2023

The Chemical Record

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From 2000, our two research groups independently and simultaneously designed and developed a novel family of electrophilic fluorinating reagents based on the use of Cinchona alkaloids. The chiral N‐fluoro ammonium salts demonstrated the highest efficiency compared to prior art in enantioselective electrophilic fluorination for a wide range of substrates. In this account, we tell our respective stories, how the same idea germinated in our laboratories, the characterization of the chiral reagents, the use in stoichiometric quantity then the development of a catalytic version, the application to the synthesis of chiral fluorinated molecules of pharmaceutical interest, and finally the exploitation of our reagents by other teams and for other applications.

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Section: The Birth Of An Ideamentioning

confidence: 89%

N‐Fluoro Ammonium Salts of Cinchona Alkaloids in Enantioselective Electrophilic Fluorination

Shibata

Cahard

2023

The Chemical Record

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“…Tetraalkylammonium fluoride has, in particular, been an important reagent in this field for many years, despite its disadvantages like decomposition upon drying [10,11]. Today, more selective and safer materials can be used, e.g., the commercially available “selectfluor” fluoridation agents comprised of diazobicyclo octane [12]. …”

Section: Introductionmentioning

confidence: 99%

Simple One-Pot Syntheses and Characterizations of Free Fluoride- and Bifluoride-Containing Polymers Soluble in Non-Aqueous Solvents

et al. 2016

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One of the problems that arise with bifluoride- or fluoride-containing compounds is their poor solubility in non-aqueous solvents. We report herein a facile one-pot synthesis and the chemical analysis of fluoride/bifluoride-containing polymers, which are soluble in MeCN. Different polymers, such as Polyvinylacetate or Polyethylene imine and saccharides, such as maltodextrin, were complexed with ammonium (bi)fluoride using hydrogen bonds to form the desired (bi)fluoride-containing compounds. The newly formed hydrogen bonding (bi)fluoride-doped polymer matrices were analyzed using infrared and nuclear magnetic resonance spectroscopies, and X-ray diffraction. The promising materials also underwent impedance spectroscopy, conductivity measurements and preliminary tests as electrolytes for room temperature fluoride ion batteries along with an analysis of their performance.

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ChemInform Abstract: 1‐Alkyl‐4‐fluoro‐1,4‐diazoniabicyclo(2.2.2)octane Salts: A Novel Family of Electrophilic Fluorinating Agents.

Cited by 2 publications

References 1 publication

N‐Fluoro Ammonium Salts of Cinchona Alkaloids in Enantioselective Electrophilic Fluorination

N‐Fluoro Ammonium Salts of Cinchona Alkaloids in Enantioselective Electrophilic Fluorination

Simple One-Pot Syntheses and Characterizations of Free Fluoride- and Bifluoride-Containing Polymers Soluble in Non-Aqueous Solvents

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