2014
DOI: 10.1002/asia.201403052
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Regioselective CH Imidation of Five‐Membered Heterocyclic Compounds through a Metal Catalytic or Organocatalytic Approach

Abstract: An efficient method for the synthesis of 2-amino and β-amino five-membered heterocyclic derivatives that are closely related to a variety of biologically active natural products is described. Regioselectivity was achieved through a metal catalytic or organocatalytic approach. Preliminary studies on the reaction mechanism suggest a radical imidation pathway; however, further studies are needed to verify the mechanism.

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Cited by 30 publications
(6 citation statements)
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“…Conventionally, transition metal-catalyzed aminations of carbon–halogen bonds in halogenated arenes are largely regarded as reliable and versatile . As an emerging synthetic route, transition metal-catalyzed aryl C–H aminations have become an alternative to conventional amination. However, this approach is still in its infancy and has several disadvantages such as (1) the necessity for a directing group, (2) the requirement for a large excess of arene, and (3) limited substrate scope especially for 5-membered heterocycles .…”
mentioning
confidence: 99%
“…Conventionally, transition metal-catalyzed aminations of carbon–halogen bonds in halogenated arenes are largely regarded as reliable and versatile . As an emerging synthetic route, transition metal-catalyzed aryl C–H aminations have become an alternative to conventional amination. However, this approach is still in its infancy and has several disadvantages such as (1) the necessity for a directing group, (2) the requirement for a large excess of arene, and (3) limited substrate scope especially for 5-membered heterocycles .…”
mentioning
confidence: 99%
“…Sun and Zhao reported copper-catalyzed C–H/N–H-type imidation of furans, thiophenes, and pyrroles by using t BuOOH as an oxidant (Scheme .) . Li and Duan showed the same reaction with nickel catalyst .…”
Section: C–h Amination Of 5-membered Heteroarenesmentioning
confidence: 60%
“…Sun and Zhao reported copper-catalyzed C−H/N−H-type imidation of furans, thiophenes, and pyrroles by using tBuOOH as an oxidant (Scheme 16.). 44 Li and Duan showed the same reaction with nickel catalyst. 45 Heterogeneous γ-MnO 2 -catalyzed oxidative amination of benzoxazoles was reported.…”
Section: ■ Introductionmentioning
confidence: 68%
“…From this point the synthesis of C-N or C-O by the activation of C-H bond is very important. Xin W. and co-worker [72] synthesis new heterocyclic by the amination of five member heterocyclic ring with Metal or organocatalysis. To optimize the reaction of 2-Acetylfuran 10 (0.5 mmol) and saccharin (2.0 equiv) as substrates, under atmospheric conditions in the presence of CuCl (10 mol%) and select Fluor (2.0 equiv) at 120 o C for 6 h with nitro methane (CH3NO2) as the solvent, the desired imidation product 1-(5-aminofuran-2-yl)ethanone 11 was obtained in 55 % yield (Table 1, entry 1).…”
Section: Heterocyclic C-n Bonds Formationmentioning
confidence: 99%