ChemInform Abstract: Potassium Trifluoroborate Salts as Convenient, Stable Reagents for Difficult Alkyl Transfers

Molander, Gary A.; Sandrock, Deidre L.

doi:10.1002/chin.201019250

Cited by 26 publications

(36 citation statements)

References 42 publications

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“…Transformations involving organoboron substrates are fundamental in any organic chemist’s toolkit. Specifically, the Suzuki–Miyaura cross-coupling reaction has become a “household” name in organic chemistry and continues to demonstrate the usefulness of organoboron substrates as synthetic intermediates . Such cross-coupling reactions are ubiquitous and allow for the construction of otherwise difficult C–C bonds.…”

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confidence: 99%

Route to Air and Moisture Stable β-Difluoroboryl Acrylamides

et al. 2019

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A method for the preparation of air stable difluoroboryl acrylamides is reported. In contrast to the ubiquitous organotrifluoroborate salts, difluoroboryl acrylamides are relatively nonpolar and are readily purified by silica chromatography. Difluoroboryl acrylamides serve as efficient substrates in cross-coupling reactions to afford the corresponding trisubstituted acrylamides in good to excellent yields. The utility of the difluoroboryl group in various chemical transformations is presented.

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confidence: 99%

Route to Air and Moisture Stable β-Difluoroboryl Acrylamides

et al. 2019

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“…18 Despite the excellent reactivity reported, the use of arylethynyltrifluoroborates as dienophiles for IEDDA ligation under bioorthogonal conditions remains unexplored because of water incompatibility. Potassium trifluoroborate is a convenient functional group in organic chemistry, in particularly for Suzuki-Miyaura couplings 19 because it is moisture and air stable and inert to strongly oxidative conditions. 20 Besides, the potassium trifluoroborate form is most often a solid soluble in aqueous media, making it easy to handle and store.…”

Section: Resultsmentioning

confidence: 99%

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

Guo¹,

Oliveira²,

Navo³

et al. 2019

Preprint

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Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (t1/2≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.

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“… 18 Despite its excellent reactivity, the use of arylethynyltrifluoroborates as dienophiles for IEDDA ligation has not been tried because of the high reactivity of TMSCl with many biological functional groups as well as TMSCl water incompatibility. Potassium trifluoroborate is a convenient functional group in organic chemistry, in particularly for Suzuki–Miyaura coupling reactions 19 because it is moisture and air stable and inert to strong oxidative conditions. 20 Besides, trifluoroborates are most often solids that are soluble in aqueous media, which makes them easy to handle and store.…”

Section: Introductionmentioning

confidence: 99%

Arylethynyltrifluoroborate Dienophiles for on Demand Activation of IEDDA Reactions

et al. 2021

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Strained alkenes and alkynes are the predominant dienophiles used in inverse electron demand Diels–Alder (IEDDA) reactions. However, their instability, cross-reactivity, and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for fast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g., pyridyl- to benzyl-substituents), cycloaddition kinetics can vary from fast ( k 2 = 21 M –1 s –1 ) to no reaction with an alkyne-BF 3 dienophile. The reported system was applied to protein labeling both in the test tube and fixed cells and even enabled mutually orthogonal labeling of two distinct proteins.

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ChemInform Abstract: Potassium Trifluoroborate Salts as Convenient, Stable Reagents for Difficult Alkyl Transfers

Cited by 26 publications

References 42 publications

Route to Air and Moisture Stable β-Difluoroboryl Acrylamides

Route to Air and Moisture Stable β-Difluoroboryl Acrylamides

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

Arylethynyltrifluoroborate Dienophiles for on Demand Activation of IEDDA Reactions

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