(Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes

Frohn, Hermann‐Josef; Franke, Holger; Fritzen, Petra; Bardin, V. V.

doi:10.1016/s0022-328x(99)00690-7

Cited by 118 publications

(83 citation statements)

References 17 publications

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“…Although the preparation of K[RCF=CFBF 3 ] looks at first sight like the earlier described synthesis of K[C 6 H 5±n F n BF 3 ] [1], nevertheless there are two distinctions between them. In contrast to the polyfluoroaryl-trialkoxyborane system [1], no diorganyl-(methoxy)boranes as well as diorganyldimethoxyborates were found in the polyfluoroalkenyl-B(OMe) 3 system.…”

Section: Resultsmentioning

confidence: 94%

“…(1), cis-, trans-Cl (2), cis-C 2 F 5 (3), cis-C 6 F 13 (4), trans-C 4 F 9 (5), trans-C 4 H 9 (6), trans-C 6 H 5 (7). The position of substituent R is related to the BF 3 group.…”

Section: Resultsmentioning

confidence: 99%

“…Recently we have reported a simple and convenient synthesis of potassium salts of polyfluoroaryltrifluoroborates K[C 6 H 5±n F n BF 3 ] (n = 1±5) and of perfluoroalkyltrifluoroborates K[C n F 2n+1 BF 3 ] (n = 3, 6) by the fluoridation of the corresponding dialkoxyboranes Org F B(OMe) 2 and trialkoxyborates M[Org F B(OMe) 3 ] using K[HF 2 ] [1,2]. Those intermediate boranes and borates were obtained by the reaction of fluoro-containing organomagnesium or lithium reagents with B(OAlk) 3 and used in the further synthetic route without isolation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Spectroscopic Characterization of Potassium Polyfluoroalken-1-yltrifluoroborates

Frohn¹,

Bardin

2001

Z. anorg. allg. Chem.

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The potassium fluoroborates K[RCF=CFBF 3 ] (R = F, Cl (cis-/trans-mixture), trans-C 4 F 9 , cis-C 2 F 5 , cis-C 6 F 13 , trans-C 4 H 9 , trans-C 6 H 5 ) were prepared by fluoridation (methoxide-fluoride substitution with K[HF 2 ]) of RCF=CFB(OMe) 2 and Li[RCF=CFB(OMe) 3 ] which were obtained from RCF=CFLi and B(OMe) 3 . The K[RCF=CFBF 3 ] salts were characterized by their 1 H, 11 B, 19 F NMR and IR spectra.

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Section: Resultsmentioning

confidence: 94%

“…(1), cis-, trans-Cl (2), cis-C 2 F 5 (3), cis-C 6 F 13 (4), trans-C 4 F 9 (5), trans-C 4 H 9 (6), trans-C 6 H 5 (7). The position of substituent R is related to the BF 3 group.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Spectroscopic Characterization of Potassium Polyfluoroalken-1-yltrifluoroborates

Frohn¹,

Bardin

2001

Z. anorg. allg. Chem.

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“…However, it was easily synthesized via the reported aryltrifluoroborate 41 (Scheme 7). [29] With the required borates in hand, the cationic structural analogues of PHIM-based betaines 43 a-44 c were easily accessible, although the yields of the intermediate P,N-ligands 45 a-c were only moderate (Scheme 8). Complexes 43 a and 43 b with X = F or H were prepared to exclude an unlikely but possible influence of this substituent on the properties of the catalysts.…”

Section: Preparation Of Cationic Analoguesmentioning

confidence: 99%

Zwitterionic Iridium Complexes with P,N‐Ligands as Catalysts for the Asymmetric Hydrogenation of Alkenes

Franzke

Pfaltz

2011

Chemistry A European J

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Several zwitterionic iridium complexes based on chiral P,N-ligands with imidazoline or oxazoline donors and anionic tetraarylborate or aryltrifluoroborate substituents have been synthesized. The corresponding cationic analogues have also been prepared, to evaluate the effect of the covalent linkage between the anion and the cationic metal complex in catalytic reactions. The respective pairs of structurally analogous precatalysts have been compared for their efficacies in the asymmetric hydrogenation of unfunctionalized olefins. In most cases, the anionic derivatization has virtually no influence on the asymmetric induction of the iridium complex. This is in accordance with X-ray structural studies, which have shown that the chiral environment of the cationic metal center is not affected by the anionic substituent. Depending on the nature of the counterion employed, the zwitterionic catalysts proved to be significantly more reactive than their cationic counterparts in nonpolar solvents.

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“…[24][25][26] Hence, the rate constants for both hydration (k 2 and k 4 ) can be expect to be much greater than k 1 . Loss of a fluoride ion from 3 and 5 is also likely to be faster than from 1 because oxygen is less electropositive than fluorine.…”

mentioning

confidence: 99%

Designing kinetically stable aryltrifluoroborates as ¹⁸F‐capture agents for PET imaging

Liu¹,

Li²,

Ting³

et al. 2015

J of Physical Organic Chem

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One‐step 18F‐radiolabeling of peptides and other large biomolecules has been challenged by a critical gap in chemical compatibility between fluoride anion, which is unreactive as a nucleophile in water, and large biomolecules such as peptides that are insoluble in dry solvents. Traditionally, this disparity has been overcome through the preliminary synthesis of an 18F‐labeled radioprosthetic group that is appended to peptides following at least one additional step. Ideally, however, peptides should be labeled in a single aqueous step. Hence, we proposed the use of arylboronic acids as captors of aqueous 18F‐fluoride ion to simplify the radiosynthesis of 18F‐aryltrifluoroborate bioconjugates. Yet, the use of aryltrifluoroborates as radioprosthetic groups can only be considered if kinetically stable ones can be designed. Herein, we discuss the kinetic and thermodynamic parameters review our previous use of a Hammett analysis that can inform the design of kinetically stable 18F‐labeled aryltrifluoroborates for use as novel radioprosthetic groups. Copyright © 2014 John Wiley & Sons, Ltd.

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(Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes

Cited by 118 publications

References 17 publications

Synthesis and Spectroscopic Characterization of Potassium Polyfluoroalken-1-yltrifluoroborates

Synthesis and Spectroscopic Characterization of Potassium Polyfluoroalken-1-yltrifluoroborates

Zwitterionic Iridium Complexes with P,N‐Ligands as Catalysts for the Asymmetric Hydrogenation of Alkenes

Designing kinetically stable aryltrifluoroborates as ¹⁸F‐capture agents for PET imaging

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(Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes

Cited by 118 publications

References 17 publications

Synthesis and Spectroscopic Characterization of Potassium Polyfluoroalken-1-yltrifluoroborates

Synthesis and Spectroscopic Characterization of Potassium Polyfluoroalken-1-yltrifluoroborates

Zwitterionic Iridium Complexes with P,N‐Ligands as Catalysts for the Asymmetric Hydrogenation of Alkenes

Designing kinetically stable aryltrifluoroborates as 18F‐capture agents for PET imaging

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Designing kinetically stable aryltrifluoroborates as ¹⁸F‐capture agents for PET imaging