A1 Journal article (refereed)
1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions (2021)
Schöbel, J.-H., Elbers, P., Truong, K.-N., Rissanen, K., & Bolm, C. (2021). 1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions. Advanced Synthesis and Catalysis, 363(5), 1322-1329. https://doi.org/10.1002/adsc.202001505
JYU authors or editors
Publication details
All authors or editors: Schöbel, Jan-Hendrik; Elbers, Philipp; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten
Journal or series: Advanced Synthesis and Catalysis
ISSN: 1615-4150
eISSN: 1615-4169
Publication year: 2021
Publication date: 14/01/2021
Volume: 363
Issue number: 5
Pages range: 1322-1329
Publisher: Wiley-VCH Verlag
Publication country: Germany
Publication language: English
DOI: https://doi.org/10.1002/adsc.202001505
Publication open access: Openly available
Publication channel open access: Partially open access channel
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/74041
Additional information: This article also appears in: Hot Topic: C-H Activation
Abstract
Three‐dimensional aza‐analogues of 1,2‐benzothiazine 1,1‐dioxides have been prepared from sulfonimidamides. Two different protocols are presented. The first is a rhodium‐catalyzed annulation reaction with alpha‐sulfonyloxyketones leading to 4 unsubstituted benzothiazine derivatives. By selective bromination with NBS the heterocyclic ring can further be functionalized. In the second approach, an iridium catalyst is applied under solvent‐free mechanochemical conditions providing products with 3,4‐disubstituted thiazine rings from diazoketo esters and diazoketo sulfones.
Keywords: organic compounds; sulphur compounds; chemical synthesis; catalysis
Free keywords: 1,2-benzothiazine; C−H activation; mechanochemistry; iridium catalysis; rhodium catalysis; sulfonimidamide
Contributing organizations
Ministry reporting: Yes
Reporting Year: 2021
JUFO rating: 2
