Nickel-Catalyzed β-Regioselective Amination/Cyclization of Ynamide-Nitriles with Amines: Synthesis of Functionalized 3-Aminoindoles and 4-Aminoisoquinolines

Hu, Xiaoping; Xie, Xin; Gan, Yi; Wang, Gaonan; Liu, Yuanhong

doi:10.1021/acs.orglett.0c04278

Cited by 13 publications

(7 citation statements)

References 38 publications

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“…In 2021, Liu et al described a unique and efficient method for the synthesis of 3-aminoindoles 181 via regio-selective cyclization of ynamide-nitriles 179 and amines 180 (Scheme 60). 71 The electron-donating substituents on the amine significantly increased its nucleophilicity, which elevated its reactivity. para -Substitution with an N , N -dimethyl group resulted in a reduced yield due to the coordinating ability of nitrogen being reduced with the metal.…”

Section: Various Transition Metal-catalysed Unusual Reactions Of Alkynesmentioning

confidence: 99%

Diverse reactivity of alkynes in C–H activation reactions

et al. 2022

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Section: Various Transition Metal-catalysed Unusual Reactions Of Alkynesmentioning

confidence: 99%

Diverse reactivity of alkynes in C–H activation reactions

et al. 2022

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“…In 2021, Liu et al described a unique and efficient method for the synthesis of 3-aminoindoles 177 via regio-selective cyclization of ynamide-nitriles 175 and amines 174 59). 70 The electron-donating substituents on the amine significantly increased its nucleophilicity, which elevated its reactivity. para-Substitution with an N,Ndimethyl group resulted in a reduced yield due to the coordinating ability of nitrogen being reduced with the metal.…”

Section: Scheme 58a Cobalt Catalyzed Regioselective C(4)-h Functional...mentioning

confidence: 99%

Reactivity of Alkynes with M-C Bonds generated through C-H Activation

Banjare

Mahulkar

Nanda

et al. 2022

Preprint

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Transition metal-catalyzed C-H activation and functionalization with various coupling partners is a well-explored area of research. Among the various coupling partners used, alkynes occupy a prominent position on account of their varied reactivity. Due to their low steric demand and a high degree of unsaturation they effectively overlap with metal d-orbitals and form multiple bond-forming events giving rise to complex skeletons that are otherwise challenging to synthesize. This makes alkyne one of the most successful coupling partners in terms of the number of useful transformations. Remarkably, by changing the reaction conditions and transition-metals from 5d to 3d, the behaviors of alkynes also change. Despite enormous explorations with alkynes, there are still a lot more possible ways by which alkynes can be made to react with M-C bonds generated through C-H activation. Especially with the development of new high and low valent first-row metal catalysts, there is plenty of scope for this chemistry to evolve as one of the most explored areas of research in coming years. Therefore, a review on this topic is both timely and useful for synthetic chemists who are working in this area. In this review, we have highlighted the diverse reactivity of alkynes with various transition metals and their applications along with some of our thoughts on future prospects.

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“…9 Thereafter, Liu and co-workers established an interesting nickel-catalyzed protocol for easy access to 3-aminoindoles and 4-aminoisoquinoline derivatives when aromatic amines reacted with ynamide-nitriles. 10 Herein, we illustrate for the first time a unique catalytic combination comprising inexpensive Cu(II) and Zn(II) salts for the synthesis of substituted 1H-pyrrolo[3,2-c]quinolines in a single-step.…”

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confidence: 99%

“…Next, the cyano group in intermediate II might be activated by Zn(OTf) 2 through coordination to form intermediate III. 10 Later, intramolecular nucleophilic attack by enamine to the Zn(II)-activated CN bond in III produces intermediate IV. Subsequently, Cu(II)-catalyzed 5-endo-dig cyclization generates V, which upon protodemetallation delivers the final product 3.…”

mentioning

confidence: 99%