Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho-Aryl and alpha-Alkyl Units Enabled by a Unique Carbanion Transmetalation
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F14%3A10277921" target="_blank" >RIV/00216208:11310/14:10277921 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/14:00427704
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201301553" target="_blank" >http://dx.doi.org/10.1002/ejoc.201301553</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201301553" target="_blank" >10.1002/ejoc.201301553</a>
Alternative languages
Result language
angličtina
Original language name
Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho-Aryl and alpha-Alkyl Units Enabled by a Unique Carbanion Transmetalation
Original language 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 isdescribed. 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.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GAP207%2F11%2F1598" target="_blank" >GAP207/11/1598: A New Carbanion Rearrangement and Its Application in Organic Synthesis</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
neuveden
Issue of the periodical within the volume
7
Country of publishing house
DE - GERMANY
Number of pages
16
Pages from-to
1461-1476
UT code for WoS article
000331612600016
EID of the result in the Scopus database
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