Observation of the Chelate Effect with a Bidentate Lewis Acid, F2BCH2CH2BF2

Shriver, Duward F.; Biallas, Michael J.

doi:10.1021/ja00981a007

Cited by 109 publications

(58 citation statements)

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“…[17] The reactions of a bidentate version of the quintessential boron-based Lewis acid (BF 3 ) with simple Lewis bases and anions were investigated. They found that F 2 BCH 2 CH 2 BF 2 , prepared by mixing ethylene and B 2 F 4 at low temperature, [18] did not readily chelate neutral bases, but that anions such as OMe Ϫ were bound by both borane centers.…”

Section: History Of Highly Lewis Acidic Organodiboryl Compoundsmentioning

confidence: 99%

“…The pioneering work of Shriver, [17] Köster, [22] Siebert, [23] and Kaufmann [24,25] described above provides obvious choices for a two-carbon linker for highly Lewis acidic, chelating organodiboryls: saturated alkyl, cis-alkenyl, and 1,2-phenylene. As the foregoing discussion has highlighted, saturated alkyl backbones are generally problematic due to the facility of retrohydroboration reactions.…”

Section: B(ar F ) 2 Units Bridged By Two Atomsmentioning

confidence: 99%

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Highly Lewis Acidic Bifunctional Organoboranes

Piers

Irvine

Williams

2000

Eur. J. Inorg. Chem.

132

106

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Chelating Lewis acids have not been developed to the same degree as multidentate Lewis bases. Nonetheless, such compounds have attracted interest due to their potential for the enhanced activation of basic substrates and the selective binding of anions. Organodiboryl compounds form a class of bidentate Lewis acids which have a long, but relatively underdeveloped history. Many examples exist where donor groups on boron serve to stabilize the Lewis acid centers. More recently, advances in the chemistry of diboryls with highly Lewis acidic boron centers substituted with perfluoroaryl groups have been made. In particular, compounds of general formula (F5C6)2B−linker−B(C6F5)2 have been prepared and their chemistry examined. In this Microreview, we survey the classes of bifunctional boron Lewis acids known, including their synthesis, properties and anion binding chemistry. Particular emphasis is placed on the role these Lewis acids play in olefin polymerization catalyst generation from simple metallocene precursors.

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Section: History Of Highly Lewis Acidic Organodiboryl Compoundsmentioning

confidence: 99%

Section: B(ar F ) 2 Units Bridged By Two Atomsmentioning

confidence: 99%

Highly Lewis Acidic Bifunctional Organoboranes

Piers

Irvine

Williams

2000

Eur. J. Inorg. Chem.

132

106

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“…Diffusion-ordered NMR spectroscopy (DOSY) suggested that, in solution, 1:1 receptor:halide complexes predominated, rather than the 2:2 complexes observed by X-ray crystallography. Neither the imidazolium 11d 2+ nor the chloroimidazolium 11a 2+ showed emission responses upon anion addition, although 1 , each bearing a single haloimidazolium moiety (Fig. 7) [53].…”

Section: Anion Recognition With Cationic Halogen Bond Donorsmentioning

confidence: 99%

“…Research on anion recognition chemistry can be traced back to the late 1960s and 1970s [1][2][3], and the field remains a topical and active one [4]. The prospects of gaining insight into the thermodynamics of noncovalent interactions and solvation/desolvation phenomena, and of developing new tools for anion analysis, separation, and sequestration continue to motivate research in this area.…”

Section: Introductionmentioning

confidence: 99%

Anion Recognition in Solution via Halogen Bonding

Taylor

2014

Topics in Current Chemistry

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An overview of the interactions between anions and electron-deficient, covalently bound halogens is presented. It might be anticipated that species such as halides and oxoanions would be good acceptors of halogen bonds because of their relatively high charge densities and nucleophilicities. The stabilities of the trihalide anions X3 (-) provide a clear indication that this is indeed the case. The thermodynamics of formation of the trihalides, and of analogous complexes between anions and monodentate haloorganics in organic solvent, are discussed in detail. Although the incorporation of multiple interacting groups to achieve high guest affinity has been a key principle of supramolecular chemistry for decades, it is only recently that multidentate halogen bond donors capable of anion recognition have been reported. This contribution highlights the range of architectures that have been employed as the basis for multidentate halogen bond donor design. Examples of selective and high-affinity anion recognition through halogen bonding, including implementations in polar, protic media, are discussed.

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“…Though rarely encountered in synthetic chemistry, neutral [8][9][10][11][12][13][14][15][16][17][18][19][20][21] and cationic [22][23][24][25][26][27] bidentate Lewis acids often exhibit striking reactivity. In FLP chemistry, C 10 H 6 (B(C 6 F 5 ) 2 ) 2 has been utilized by Berke and co-workers 28 for hydrogen activation and hydrogenation catalysis.…”

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confidence: 99%

Synthesis of a diboryl-N-heterocycle and its conversion to a bidentate cationic Lewis acid

Farrell

Stephan

2015

Chem. Commun.

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Sequential reaction of 2-lithio-1-methylimidazole with 9-borabicyclo[3.3.1]nonane (9-BBN) dimer and 9-Cl-9-BBN yields diboryl-N-heterocycle C4H5N2(H)(BC8H14)2 (1). Reaction of 1 with I2 results in the net substitution of chelated hydride for a singly boron-bound iodide to produce C4H5N2(I)(BC8H14)2 (2). Conversely, reaction of 1 with [Ph3C][B(C6F5)4] results in the formation of the bidentate cationic Lewis acid [(C4H5N2)(BC8H14)2][B(C6F5)4] (3). Compound 3 catalyzes the hydrogenation of N-benzylidene-tert-butylamine at room-temperature.

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Observation of the Chelate Effect with a Bidentate Lewis Acid, F₂BCH₂CH₂BF₂

Cited by 109 publications

References 0 publications

Highly Lewis Acidic Bifunctional Organoboranes

Highly Lewis Acidic Bifunctional Organoboranes

Anion Recognition in Solution via Halogen Bonding

Synthesis of a diboryl-N-heterocycle and its conversion to a bidentate cationic Lewis acid

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