Article
Chemistry, Inorganic & Nuclear
Geanne M. R. Boston, Hendrik M. Philipp, Holger Butenschoen
Summary: Different types of sulfonates undergo distinct rearrangements under comparable reaction conditions, yielding different products and reaction efficiencies. These findings may provide insights for the development of novel organic synthesis reactions.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Simone Ghinato, Federica De Nardi, Paola Bolzoni, Achille Antenucci, Marco Blangetti, Cristina Prandi
Summary: This paper reports a straightforward and efficient method utilizing lithium amide as a metalating agent to promote the metalation/anionic Fries rearrangements of O-aryl carbamates, under aerobic/ambient-friendly reaction conditions. This method enables the sustainable preparation of salicylamide derivatives with high levels of chemoselectivity within ultrafast reaction times, working at room temperature in the presence of air/moisture and using environmentally responsible cyclopentyl methyl ether as a solvent. Furthermore, the regioselective manipulation of O-2-tolyl carbamates has been achieved using interchangeably alkyllithiums or lithium amides, with an unexpected beneficial contribution from the utilization of biorenewable protic eutectic mixtures as non-innocent reaction media.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Andreas Hess, Jan P. Prohaska, Sabrina B. Doerrich, Florian Trauner, Ferdinand H. Lutter, Sebastien Lemaire, Simon Wagschal, Konstantin Karaghiosoff, Paul Knochel
Summary: A new toluene-soluble reagent, sBu(2)Mg, has been developed for regioselective ortho-magnesiations of various N-arylated pyrazoles and 1,2,3-triazoles, as well as arenes with specific directing groups. The resulting diarylmagnesium reagents can be further functionalized and double ortho,ortho'-magnesiations can be achieved by repeating the magnesiation/electrophile trapping sequence, allowing for the preparation of valuable functionalized arenes.
Review
Chemistry, Organic
Hans-Joachim Gais
Summary: Sulfoximines are a class of compounds with interesting properties such as Bronsted and Lewis basicity, nucleophilicity, C-H acidity, N-H acidity, hydrogen-bond acceptor capability and chirality, which have attracted renewed interest recently for their potential in drug candidates. The synthesis and functionalization of sulfoximines, including arene ortho-lithiation and synthesis of ortho-substituted S-aryl sulfoximines, are currently popular research topics. Comparison with sulfone group shows both groups are equally effective in directing arene ortho-lithiation, with the ability to produce various compounds with different rearrangements and reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Geanne M. R. Boston, Holger Butenschon
Summary: In this study, the first syntheses of triflate substituted cobaltocenium cations were reported. The reaction with triflic anhydride yielded the triflate substituted cobaltocenium cations, and further treatment with lithium diisopropylamide led to the first anionic thia-Fries rearrangements of cobaltocenium complexes.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuya Okui, Yuto Yasuda, Atsunori Mori, Kentaro Okano
Summary: A total synthesis of lamellarins U and A3 is described. The synthesis involves the interruption of a halogen dance reaction and the incorporation of an aryl group onto the pyrrole ring. The final products are obtained through a series of reactions.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Applied
Markus Jakobi, Bouthayna Zilate, Christof Sparr
Summary: Photostability is crucial for the overall performance of photocatalysts. This article presents a modular and flexible synthetic approach to incorporate diarylamino moieties into organic acridinium photocatalysts, resulting in tunable redox behavior and enhanced photostability.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Paul Knochel, Kevin P. Cole
Summary: The tribute to Professor Victor Snieckus focuses on his significant contributions to the field of organic chemistry and directed ortho metalation technology.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Geanne M. R. Boston, Irmgard Frank, Holger Butenschon
Summary: Ferrocenyl triflate and 1,1'-ferrocenediyl ditriflate undergo single and double anionic thia-Fries rearrangements at low temperatures, with the latter exclusively forming the meso product. The mechanisms of these rearrangements were studied using DFT calculations, revealing the unprecedented meso diastereoselectivity of the double anionic thia-Fries rearrangement of 1,1'-ferrocenediyl ditriflate.
HELVETICA CHIMICA ACTA
(2021)
Article
Chemistry, Organic
Ibrahim D. Bori, Daniel L. Comins
Summary: The research has successfully developed an effective method for the synthesis of various substituted pyridines through directed metalation and metal-halogen exchange reactions.
