Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry

Stang, Peter J.; Hanack, Michael; Subramanian, L. R.

doi:10.1055/s-1982-29711

Cited by 537 publications

(234 citation statements)

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“…The organic layer was dried with MgSO 4 , concentrated under vacuum, and immediately carried on to the next step.…”

mentioning

confidence: 99%

“…Upon completion, the reaction was diluted with diethyl ether (25 mL) and washed with water (10 mL) and brine (10 mL). The organic layer was dried with MgSO 4 , concentrated under vacuum, and purified by flash chromatography (5:1 hexanes:ethyl acetate eluent) to yield phenol 23 (62 mg, 42% yield over two steps): R f = 0.26 (3:1 hexanes:ethyl acetate); 1 H NMR (500 MHz, CDCl 3 ) δ 7.48-7.32 (m, 10H), 6.29 (t, J = 2.1 Hz, 1H), 6.13 (d, J = 2.1 Hz, 2H), 5.17 (s, 1H), 5.00 (s, 4H); 13 …”

mentioning

confidence: 99%

“…The reaction was diluted with H 2 O (10 mL) and extracted with CH 2 Cl 2 (2 x 20 mL). The combined organic extracts were dried with MgSO 4 , concentrated under vacuum, and purified by flash chromatography Silyl aryl triflate 9. Bromophenol 24 (310 mg, 0.805 mmol) and hexamethyldisilazide (361 µL, 1.77 mmol) were combined in THF (3.2 mL).…”

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Regioselective Reactions of Highly Substituted Arynes

et al. 2010

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The fully regioselective reactivity of four new highly substituted silyl aryl triflate aryne precursors in aryne acyl-alkylation, acyl-alkylation/ condensation, and heteroannulation reactions is reported. The application of these more complex arynes provides access to diverse natural product scaffolds and obviates late-stage functionalization of aromatic rings.It has been well established that substituted arynes undergo nucleophilic attack with levels of regioselectivity dependent on the identity of substituents and their locations relative to the reactive aryne triple bond. 1 In our own investigations, we have observed fully regioselective acyl-alkylation 2 and aryne heteroannulation 3 reactions with the aryne (2) generated in situ from a 3-methoxy-substituted silyl aryl triflate (1) (Scheme 1). Each of these products (3-6) stems presumably from initial attack at C(1) of the aryne (2), which suggests that the o-methoxy substituent electronically polarizes the triple bond and sterically shields the adjacent atom to favor this reactivity. More recently, we have been able to exploit this selectivity in aryne acyl-alkylation/condensation sequences to produce either substituted hydroxynaphthoquinones (6) or hydroxyisoquinolines (5). 4 These observations led us to investigate whether more highly functionalized silyl aryl triflates would also exhibit the predictable regioselectivity seen for precursor 1.Specifically, we chose to examine whether unsymmetrically substituted polyalkyoxy silyl aryl triflates would react

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“…The organic layer was dried with MgSO 4 , concentrated under vacuum, and immediately carried on to the next step.…”

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confidence: 99%

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Regioselective Reactions of Highly Substituted Arynes

et al. 2010

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“…Bis(pinacolato)diboron [13], vinyl triflates [14], potassium phenoxide [20], and potassium 2-methylphenoxide [21] were prepared by the reported procedures. Solvents were purified by distillation from appropriate drying agents.…”

Section: Materials and Reagentsmentioning

confidence: 99%

“…In connection with our interest in the synthesis of organoboron compounds via the cross-coupling reaction of diborons with organic electrophiles [8] including aryl [8,9], vinyl [8,10], allyl [8,11], and benzyl [8,12] halides or triflates, we wish to disclose here a palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron [13] (pin 2 B 2 , pin = Me 4 C 2 O 2 ) 1 with vinyl triflates [14] 2 to yield the corresponding β-boryl-α,β-unsaturated carbonyl compounds 3 (Scheme 1) [15]. <<Scheme 1>>…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Cross‐Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates β‐Substituted by a Carbonyl Group: Efficient Synthesis of β‐Boryl‐α,β‐unsaturated Carbonyl Compounds and Their Synthetic Utility.

et al. 2004

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Activation of Aryl and Vinyl Triflates by Palladium and Electron Transfer – Electrosynthesis of Aromatic and α,β-Unsaturated Carboxylic Acids from Carbon Dioxide

Jutand¹,

Négri²

1998

Eur. J. Org. Chem.

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The electrochemical reduction of aryl and vinyl triflates in the presence of CO2 and a catalytic amount of palladium results in the formation of aromatic and α,β‐unsaturated carboxylic acids. Aryl and vinyl triflates usually undergo palladium‐catalysed cross‐coupling reactions with nucleophiles. Their reactivity has been reversed in the presence of an electron source, so that they react with electrophiles such as CO2. The reaction proceeds through an activation of the C–O bond of the aryl or vinyl triflate by oxidative addition to a palladium(0) complex, followed by an activation by electron transfer of the thus formed aryl‐ or vinylpalladium(II) complexes.

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Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry

Cited by 537 publications

References 0 publications

Regioselective Reactions of Highly Substituted Arynes

Regioselective Reactions of Highly Substituted Arynes

Palladium‐Catalyzed Cross‐Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates β‐Substituted by a Carbonyl Group: Efficient Synthesis of β‐Boryl‐α,β‐unsaturated Carbonyl Compounds and Their Synthetic Utility.

Activation of Aryl and Vinyl Triflates by Palladium and Electron Transfer – Electrosynthesis of Aromatic and α,β-Unsaturated Carboxylic Acids from Carbon Dioxide

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