Primary and Secondary Amines by Flavin-Photocatalyzed Consecutive Desulfonylation and Dealkylation of Sulfonamides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F23%3A00579795" target="_blank" >RIV/61388963:_____/23:00579795 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/23:43928497
Result on the web
<a href="https://doi.org/10.1002/adsc.202300843" target="_blank" >https://doi.org/10.1002/adsc.202300843</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.202300843" target="_blank" >10.1002/adsc.202300843</a>
Alternative languages
Result language
angličtina
Original language name
Primary and Secondary Amines by Flavin-Photocatalyzed Consecutive Desulfonylation and Dealkylation of Sulfonamides
Original language description
Alkane-, arene-, and perfluoroalkanesulfonyl groups are widely used in organic synthesis to protect amino functionalities or to facilitate their installation. Protection of amino functions by a sulfonyl group to form sulfonamides is advantageous as they are easy to purify and tolerate various reaction conditions. On the other hand, sulfonyl group removal is difficult. Herein, we present a versatile metal-free photocatalytic reductive method for desulfonylation of sulfonamides and aryl sulfonates to the parent amines mediated by flavin derivatives, namely deazaisoalloxazines and deazaalloxazines, and visible light. Photocatalysis with 5-deazalloxazines is shown to even mediate the cleavage of perfluoroalkanesulfonamides (triflylamides and nonaflylamides), which is significantly more difficult than that of other sulfonamides and has previously not been achieved by photochemical means. The method is shown to perform consecutive desulfonylation and dealkylation of N-alkyl-N-phenylperfluoroalkanesulfonamides affording primary anilines. This occurs via consecutive reductive and oxidative catalytic cycles mediated by the flavin catalyst. The perfluoroalkylsulfonyl group fulfils a dual role serving as a protecting group and, after removal by the reductive cycle, as the species driving the oxidative dealkylation reaction.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GF21-14200K" target="_blank" >GF21-14200K: Tailoring flavins for organic photocatalysis</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Advanced Synthesis & Catalysis
ISSN
1615-4150
e-ISSN
1615-4169
Volume of the periodical
365
Issue of the periodical within the volume
24
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
4662-4671
UT code for WoS article
001102447100001
EID of the result in the Scopus database
2-s2.0-85177467751