Synthesis of Pyridinylpyrrole Derivatives via the Palladium-Catalyzed Reaction of Acetylpyridines with Methyleneaziridines

“…A variety of 1,2,4-trisubstituted pyrroles 3 - 408 , containing aromatic or heteroaromatic substituents, can be synthesized in good yields using this efficient methodology (Scheme ). Definitely, the high acidity of the α-C–H bond in the carbonyl compound is essential for this transformation …”

Section: Synthesis Of Pyrrolesmentioning

confidence: 99%

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

et al. 2013

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“…In 2004, Yamamoto and co-workers disclosed a Pd(0)-catalysed C-H activation of methyl ketones such as acetylpyridines in the coupling with methyleneaziridines (Scheme 14). 18 The coupling afforded substituted pyridylpyrroles via transannulation. Besides acetylpyridines, simple acetophenone is also a viable substrate.…”

Section: C-h Activation Leading To the Formation Of A M-c Bond That I...mentioning

confidence: 99%

Transition metal-catalysed couplings between arenes and strained or reactive rings: combination of C–H activation and ring scission

Wang

2016

Chem. Soc. Rev.

317

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Organic transformations that involve direct functionalization of C-H bonds represent an attractive synthetic strategy that maximizes atom- and step-economy. With the generally high stability of C-H bonds, these processes have mostly required harsh reaction conditions, in combination with the necessity of activation of the C-H substrates and/or the coupling partners. As a class of activated coupling partners, strained or reactive rings exhibited high activity in the coupling with aryl and alkyl C-H bonds. Such a high reactivity of the rings allowed the facile construction of various new structural platforms via coupling with scission of the ring structures. The combination of C-H activation and scission of the rings allowed for applications of a broader scope of C-H bonds, including those less reactive alkyl ones. This synthetic diversity of these rings has been realized owing to the intrinsically different mechanisms of the interactions of transition metal catalysts and the strained/reactive rings.

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“…Finally, in addition to our own work highlighted herein, recent notable contributions have emerged from the laboratories of Yamamoto. He has shown that methyleneaziridines undergo a number of interesting palladiumcatalysed transformations including hydrocarbonation reactions, 66,67 ring expansions 68 and ring-opening reactions. 69…”

Section: Scheme 26 Piperidine Synthesis By Radical Rearrangementsmentioning

confidence: 99%