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Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation

Abstract:
We report a route to benzosultams that exploits the palladium-catalysed aminsulfonylation of alkenyl iodides as the initial step. An (Z)-configured alkenyl iodide substrate is combined with DABSO, a N,N-dialkylhydrazine nucleophile and a palladium(0) catalyst to achieve aminsulfonylation. A second palladium(0)-catalysed transformation, this time intramolecular, leads to benzosultam formation. Good variation of the starting alkenyl iodides is possible. A related SNAr route was also explored, but was shown to be less efficient.
Publication status:
Published
Peer review status:
Peer reviewed

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Role:
Author
ORCID:
0000-0002-0636-6471
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Name:
Engineering and Physical Sciences Research Council
Grant:
EP/K00803X/1
Publisher:
Elsevier
Journal:
Tetrahedron More from this journal
Volume:
83
Article number:
131988
Publication date:
2021-02-03
Acceptance date:
2021-01-26
DOI:
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
1161186
Local pid:
pubs:1161186
Deposit date:
2021-02-12

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