ChemInform Abstract: Considered Electrophilic Aromatic Substitution. Part 66. Regioselective Nitration of Arylboronic Acids.

Salzbrunn, Stefan; Simon, Juergen; Prakash, G. K. Surya; Petasis, Nicos A.; Oláh, George A.

doi:10.1002/chin.200105075

Cited by 8 publications

(10 citation statements)

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“…Therefore, it seems unlikely that the reaction proceeds by a radical mechanism, 13 and perhaps an electrophilic aromatic substitution with ipso attack is more likely (Scheme 2). 14 …”

Section: Resultsmentioning

confidence: 99%

Metal-Free Chlorodeboronation of Organotrifluoroborates

Molander

Cavalcanti

2011

J. Org. Chem.

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“…Therefore, it seems unlikely that the reaction proceeds by a radical mechanism, 13 and perhaps an electrophilic aromatic substitution with ipso attack is more likely (Scheme 2). 14 …”

Section: Resultsmentioning

confidence: 99%

Metal-Free Chlorodeboronation of Organotrifluoroborates

Molander

Cavalcanti

2011

J. Org. Chem.

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“…[31] In the presence of Crivello’s reagent (mixture of ammonium nitrate/trifluoroacetic anhydride), arylboronic acids were converted to the corresponding nitroarenes in moderate yields (Scheme 16). Despite carefully regulating the reaction temperature at −35 °C, the by-product from undesired di-nitration could not be suppressed.…”

Section: Carbon-nitrogen Bond Formationmentioning

confidence: 99%

Transition Metal‐Free ipso‐Functionalization of Arylboronic Acids and Derivatives

Zhu

Falck

2014

Adv Synth Catal

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Arylboronic acids and their derivatives have been widely exploited as important synthetic precursors in organic synthesis, materials science, and pharmaceutical development. In addition to numerous applications in transition-metal-mediated cross-coupling reactions, transition-metal-free transformations involving arylboronic acids and derivatives have recently received a surge of attention for converting the C-B bond to C-C, C-N, C-O, and many other C-X bonds. Consequently, a wide range of useful compounds, e.g., phenols, anilines, nitroarenes, and haloarenes, have been readily synthesized. Amongst these efforts, many versatile reagents have been developed and a lot of practical approaches demonstrated. The research in this promising field is summarized in the current review and organized on the basis of the type of bonds being formed.

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“…The ipso -substitution of arylboron species, as previously demonstrated for halogenation 21 and nitration 22 of arylboronic acids, provides a potential means to accomplish this goal. Recently, our group published the chlorodeboronation of aryl and heteroaryltrifluoroborates, which most likely occurs by an ipso- substitution (Scheme 2).…”

Section: Introductionmentioning

confidence: 95%

Nitrosation of Aryl and Heteroaryltrifluoroborates with Nitrosonium Tetrafluoroborate

Molander

Cavalcanti

2012

J. Org. Chem.

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Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF4). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.

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ChemInform Abstract: Considered Electrophilic Aromatic Substitution. Part 66. Regioselective Nitration of Arylboronic Acids.

Cited by 8 publications

References 0 publications

Metal-Free Chlorodeboronation of Organotrifluoroborates

Metal-Free Chlorodeboronation of Organotrifluoroborates

Transition Metal‐Free ipso‐Functionalization of Arylboronic Acids and Derivatives

Nitrosation of Aryl and Heteroaryltrifluoroborates with Nitrosonium Tetrafluoroborate

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