Some Salts of Trifluoromethylfluoroboric Acid<sup>1,2</sup>

Chambers, Richard D.; Clark, H. C.; Willis, Christopher J.

doi:10.1021/ja01505a007

Cited by 101 publications

(52 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…With the exception of trifluoromethylfluoroborate salts M [(CF 3 ) n BF 4±n ] (n = 1±3) [2,3] perfluoroalkylfluoroborates M [Alk F BF 3 ] are still unknown. The synthesis of trifluoromethylfluoroborates is based on the CF 3 -group transfer from CF 3 SnMe 3 to BF 3 in CCl 4 followed by treatment with aq.…”

mentioning

confidence: 99%

See 1 more Smart Citation

A Preparative Method for Perfluoroalkyltrifluoroborates and Perfluoroalkyldifluoroboranes

Frohn¹,

Bardin

2001

Z. anorg. allg. Chem.

View full text Add to dashboard Cite

A convenient new preparative method for the unknown class of perfluoroalkyltrifluoroborates K[C n F 2n+1 BF 3 ] and perfluoroalkyldifluoroboranes C n F 2n+1 BF 2 (n > 1) is elaborated. The perfluoroalkyl group is introduced into the boric acid ester by using C n F 2n+1 MgBr. Treatment with K[HF 2 ] and HF aq results in K[C n F 2n+1 BF 3 ] which can be defluoridated by AsF 5 to the corresponding boranes C n F 2n+1 BF 2 .

show abstract

mentioning

confidence: 99%

“…The synthesis of trifluoromethylfluoroborates is based on the CF 3 -group transfer from CF 3 SnMe 3 to BF 3 in CCl 4 followed by treatment with aq. KF [2,3]. Using this procedure [(CF 3 ) n BF 4±n ] ± salts with n = 1, 2 were obtained.…”

mentioning

confidence: 99%

A Preparative Method for Perfluoroalkyltrifluoroborates and Perfluoroalkyldifluoroboranes

Frohn¹,

Bardin

2001

Z. anorg. allg. Chem.

View full text Add to dashboard Cite

show abstract

“…[46][47][48] Boronic acids often dimerize and trimerize to form boronic acid anhydrides and boroxines, 49) which make difficulties in the direct purification and determination of exact chemical amount. On the other hand, potassium organotrifluoroborates are highly air-and moisture-stable crystalline solids [50][51][52] and more easily prepared, purified, and handled although these compounds are less soluble in organic solvents and require protic solvents for their dissolution. [46][47][48] In spite of these advantages, only two kinds of rhodium(I)-phosphine catalysts for the 1,2-addition to aldehydes with potassium organotrifluoroborates have been reported.…”

Section: Palladium-imidazolinium Carbene-catalyzed 12-addition Of Pomentioning

confidence: 99%

Development of Efficient Catalytic Arylation of Aldehydes with Thioether-Imidazolinium Carbene Ligands

Kuriyama

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Effective methods of ligand design have been highly sought due to the significant roles of ligands in controlling metal catalyses. In particular, easy-to-handle ligands to realize high reaction efficacy, substrate tolerance, and environmental friendliness are desirable. Novel bidentate ligands containing N-heterocyclic carbene and thioether moieties were developed based on findings of hemilabile coordination, whose precursors were crystalline solids stable enough to handle and store in the air. The thioether-imidazolinium carbene ligand successfully brought out high catalyst performance of palladium in the catalytic arylation of aldehydes with organoboron reagents, which tolerated a diverse range of substrates including poorly reactive, sterically hindered, and heterocyclic compounds. This process was applied to gram-scale synthesis using only water as solvent with high efficiency and also achieved the effective one-pot synthesis of 3-arylphthalides known as useful biologically active agents and important synthetic intermediates for naturally occurring compounds.

show abstract

“…(1)]. [7,8,29,30] Kürzlich konnte gezeigt werden, dass Die Synthese von Borderivaten mit mehr als zwei CF 3 -Gruppen gelingt nicht durch Trifluormethylübertragung, wenn die Lewis-Acidität der Zwischenstufe (CF 3 ) 2 BR zu groß ist. Ausgehend von Aminoboranen R 2 NBHal 2 (R = Alkyl, Hal = Cl, Br), in denen die Lewis-Acidität des B-Atoms durch den Stickstoffsubstituenten herabgesetzt ist, dagegen gelingt die Einführung von bis zu drei Trifluormethylliganden an Bor durch CF 3 -Übertragung.…”

Section: Die Synthese Von Cf 3 -B-verbindungenunclassified

Trifluormethylborane und ‐borate – neue Synthesestrategien und Anwendungen

2007

View full text Add to dashboard Cite

Mit der Synthese des [B(CF3)4]−‐Anions setzte eine neue Entwicklung im Bereich der Trifluormethylborchemie ein. Während die bisher beschriebenen (CF3)nB‐Derivate (n=1–3) ausschließlich durch die Übertragung von CF3‐Gruppen hergestellt wurden, gelang die Synthese des [B(CF3)4]−‐Anions durch die Fluorierung des [B(CN)4]−‐Anions mit ClF oder ClF3 in wasserfreier HF. Aufgrund seiner thermischen und chemischen Stabilität ist das [B(CF3)4]−‐Anion ein attraktives schwach koordinierendes Anion. In konzentrierter Schwefelsäure wird jedoch eine der vier CF3‐Gruppen zu einem CO‐Liganden solvolysiert und das neutrale Carbonylboran (CF3)3BCO erhalten. Es zeigte sich, dass diese Verbindung ein vielseitiger Synthesebaustein ist, und zahlreiche Reaktionen wurden inzwischen untersucht. Nucleophile addieren bevorzugt an das C‐Atom des CO‐Liganden. Beispiele neuer Derivate sind die Anionen [(CF3)3BCPnic]− (Pnic=N, P, As). Es ist aber auch ein Ligandenaustausch unter Abgabe von CO beispielsweise zu (CF3)3BNCH möglich. Schließlich ist (CF3)3BCO eine Komponente der konjugierten Brønsted‐Lewis‐Supersäure HF/(CF3)3BCO.

show abstract

Some Salts of Trifluoromethylfluoroboric Acid^1,2

Cited by 101 publications

References 0 publications

A Preparative Method for Perfluoroalkyltrifluoroborates and Perfluoroalkyldifluoroboranes

A Preparative Method for Perfluoroalkyltrifluoroborates and Perfluoroalkyldifluoroboranes

Development of Efficient Catalytic Arylation of Aldehydes with Thioether-Imidazolinium Carbene Ligands

Trifluormethylborane und ‐borate – neue Synthesestrategien und Anwendungen

Contact Info

Product

Resources

About

Some Salts of Trifluoromethylfluoroboric Acid1,2

Cited by 101 publications

References 0 publications

A Preparative Method for Perfluoroalkyltrifluoroborates and Perfluoroalkyldifluoroboranes

A Preparative Method for Perfluoroalkyltrifluoroborates and Perfluoroalkyldifluoroboranes

Development of Efficient Catalytic Arylation of Aldehydes with Thioether-Imidazolinium Carbene Ligands

Trifluormethylborane und ‐borate – neue Synthesestrategien und Anwendungen

Contact Info

Product

Resources

About

Some Salts of Trifluoromethylfluoroboric Acid^1,2