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Description
| - The electron-accepting sulfonyl group exhibits a strong acidifying influence on neighboring -H atoms. The Julia and related olefinations are based on this effect. Here a surprising reversal in the metalation selectivity of branched alkyl aryl sulfones is described. Such sulfones were found to initially undergo directed ortho-metalation with good regioselectivity, despite having a more acidic -H atom. The structure of the alkyl unit profoundly, but predictably, influences the regioselectivity of the attack of the base. In - and -branched ortho-(alkylsulfonyl)aryllithiums a transmetalation to the -carbanion proceeds only upon warming. Correspondingly generated ortho- or -carbanions were then selectively applied thus permitting access to synthetically interesting compound classes.
- The electron-accepting sulfonyl group exhibits a strong acidifying influence on neighboring -H atoms. The Julia and related olefinations are based on this effect. Here a surprising reversal in the metalation selectivity of branched alkyl aryl sulfones is described. Such sulfones were found to initially undergo directed ortho-metalation with good regioselectivity, despite having a more acidic -H atom. The structure of the alkyl unit profoundly, but predictably, influences the regioselectivity of the attack of the base. In - and -branched ortho-(alkylsulfonyl)aryllithiums a transmetalation to the -carbanion proceeds only upon warming. Correspondingly generated ortho- or -carbanions were then selectively applied thus permitting access to synthetically interesting compound classes. (en)
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Title
| - Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho-Aryl and alpha-Alkyl Units Enabled by a Unique Carbanion Transmetalation
- Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho-Aryl and alpha-Alkyl Units Enabled by a Unique Carbanion Transmetalation (en)
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skos:prefLabel
| - Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho-Aryl and alpha-Alkyl Units Enabled by a Unique Carbanion Transmetalation
- Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho-Aryl and alpha-Alkyl Units Enabled by a Unique Carbanion Transmetalation (en)
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skos:notation
| - RIV/00216208:11310/14:10277921!RIV15-MSM-11310___
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http://linked.open...avai/riv/aktivita
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http://linked.open...avai/riv/aktivity
| - I, P(GAP207/11/1598), Z(MSM0021620857)
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http://linked.open...iv/cisloPeriodika
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http://linked.open...vai/riv/dodaniDat
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http://linked.open...aciTvurceVysledku
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http://linked.open.../riv/druhVysledku
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http://linked.open...iv/duvernostUdaju
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http://linked.open...titaPredkladatele
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http://linked.open...dnocenehoVysledku
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http://linked.open...ai/riv/idVysledku
| - RIV/00216208:11310/14:10277921
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http://linked.open...riv/jazykVysledku
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http://linked.open.../riv/klicovaSlova
| - acidity; alkylation; deprotonation; lithiation; transmetalation; sulfones (en)
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http://linked.open.../riv/klicoveSlovo
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http://linked.open...odStatuVydavatele
| - DE - Spolková republika Německo
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http://linked.open...ontrolniKodProRIV
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http://linked.open...i/riv/nazevZdroje
| - European Journal of Organic Chemistry
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http://linked.open...in/vavai/riv/obor
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http://linked.open...ichTvurcuVysledku
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http://linked.open...cetTvurcuVysledku
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http://linked.open...vavai/riv/projekt
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http://linked.open...UplatneniVysledku
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http://linked.open...v/svazekPeriodika
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http://linked.open...iv/tvurceVysledku
| - Císařová, Ivana
- Jahn, Ullrich
- Řehová, Lucie
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http://linked.open...ain/vavai/riv/wos
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http://linked.open...n/vavai/riv/zamer
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issn
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number of pages
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http://bibframe.org/vocab/doi
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http://localhost/t...ganizacniJednotka
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