2010
DOI: 10.1002/chin.201051110
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ChemInform Abstract: Fe(II)‐Catalyzed Amination of Aromatic C—H Bonds via Ring Opening of 2H‐Azirines: Synthesis of 2,3‐Disubstituted Indoles.

Abstract: Fe(II)-Catalyzed Amination of Aromatic C-H Bonds via Ring Opening of 2H-Azirines: Synthesis of 2,3-Disubstituted Indoles. -The method tolerates a broad spectrum of functionalities and can also be used for the preparation of azaindoles such as (IV). -(JANA, S.; CLEMENTS, M. D.; SHARP, B. K.; ZHENG*, N.; Org.

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“…The reaction proceeded smoothly as indicated by TLC results and furnished two products, which were characterized as isomeric isoxazoles 3s and 5s on the basis of their spectral and analytical data (Scheme 2). 21 Obviously, 3s and 5s were formed through chemoselective rearrangement of 2H-azirine 4s, 25,26 and the selectivity might be attributed to the different reactivity of O-atom in a ketone or an amide group. 27 This finding provided an alternative protocol for the synthesis of fully substituted isoxazoles of type 3 and 5.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…The reaction proceeded smoothly as indicated by TLC results and furnished two products, which were characterized as isomeric isoxazoles 3s and 5s on the basis of their spectral and analytical data (Scheme 2). 21 Obviously, 3s and 5s were formed through chemoselective rearrangement of 2H-azirine 4s, 25,26 and the selectivity might be attributed to the different reactivity of O-atom in a ketone or an amide group. 27 This finding provided an alternative protocol for the synthesis of fully substituted isoxazoles of type 3 and 5.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…The formation of C–N bonds has attracted considerable intention in the field of organic catalysis due to the propensity of nitrogen-containing compounds to function as potential biologically active molecules, pharmaceutical agents, and novel hybrid materials. Various approaches including reductive amination, , Ullmann coupling, , and Buchwald–Hartwig coupling have been successfully devised to foment C–N coupling. Generally speaking, both noble metal (Pd) and transitional metal (Cu, Fe, Ni) molecular catalysts have been commonly employed to accomplish this with the assistance of bases and additives. Especially, ligand chelation with the metal is critical for the C–N coupling reaction. , Hence, separation of products from the reaction solution and recycling of the metal catalysts and prerequisite ligands become a challenge for the coupling reaction.…”
Section: Introductionmentioning
confidence: 99%