Iridium-Catalyzed <i>ortho</i>-C(sp<sup>2</sup>)–H Amidation of Benzaldehydes with Organic Azides

Mu, Delong; Wang, Xinmou; Chen, G.; He, Gang

doi:10.1021/acs.joc.7b00531

Cited by 54 publications

(9 citation statements)

References 52 publications

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“…Cooperative catalysis with a cationic iridium complex and 3‐trifluoromethylaniline ( cat‐28 ) promoted the mono‐C−H amidation of aromatic aldehydes with various sulfonyl azides to give the desire products ( 31 ) in moderate to high yields. Very recently, Yu and co‐workers, and Chen, He, and co‐workers also reported a similar reaction by using substituted meta ‐trifluromethylaniline catalysts.…”

Section: Arylamine−metal Cooperative Catalysismentioning

confidence: 99%

Aromatic Aminocatalysis

Zhang

Cai

et al. 2018

Chemistry An Asian Journal

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Aromatic aminocatalysis refers to transformations that employ aromatica mines, such as anilineso ra minopyridines, as catalysts. Owing to the conjugation of the amine moiety with the aromatic ring, aromatic amines demonstrate distinctive features in aminocatalysis compared with their aliphatic counterparts. For example, aromatic aminocatalysis typically proceeds with slower turnover,b ut is more active and conformationally rigid as ar esult of the stabilized aromatic imine or iminiums pecies. In fact, the advent of aromatic aminocatalysis can be traced back to before the renaissance of organocatalysis in the early 2000s. So far,aromatic aminocatalysis has been widely applied in bioconjugation reactions through transamination;i na symmetrico rganocatalysis through imine/enamine tautomerization;and in cooperative catalysis with transition metals through CÀH/CÀCa ctivation and functionalization. This Focus Review summarizes the advent of and major advances in the use of aromatic aminocatalysisi nb ioconjugation reactions and organic synthesis.

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Section: Arylamine−metal Cooperative Catalysismentioning

confidence: 99%

Aromatic Aminocatalysis

Zhang

Cai

et al. 2018

Chemistry An Asian Journal

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“…For example, Wang, Kim, and Cui reported Cp*Rh(III) or Ir(III)‐catalyzed ortho ‐amidation of aldehydes using aldimines or nitrones as ‘preinstalled directing groups’. In addition to that, Shi, Prabhu, Jiao, Rasheed, and He came up with the ‘transient directing group strategy (TDG)’ employing Rh, Ir and Ru(II) complexes for variety of C−H bond functionalizations. From a cost‐effective and sustainable point of view, there is great demand for having an improved procedure under base metal catalysis, which not only take care of the cost but also amenable to environmentally benign conditions.…”

Section: Methodsmentioning

confidence: 99%

Cp*Co(III)‐Catalyzed o‐Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Group Strategy

2020

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Transition metal‐catalyzed ortho‐selective C(sp2)−H amidation of weakly coordinating aldehydes remains limited to precious metals such as Ir, Rh, Ru, etc. Herein, we put forward a novel report on ortho‐amidation of benzaldehydes employing user‐friendly dioxazolones under cost‐effective and air‐stable Cp*Co(III) catalysis. This catalytic transformation involves transient directing group strategy to enhance the ligating capability of weakly chelating aldehydes.

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“…Shi, Chen and He have independently reported Cp*Ir(III)‐catalyzed, anilines facilitated, regioselective Csp 2 −H amidation of aldehydes with in situ generated imines as transient directing groups. For Shi's work, various aromatic aldehydes gave excellent yields, and electron‐rich aryl sulfonyl azides exhibited better efficiency than electron‐poor azides in this C−H amidation.…”

Section: C−n Bond Formationsmentioning

confidence: 99%

Recent Development on Cp*Ir(III)‐Catalyzed C−H Bond Functionalization

Ouyang

Nie

et al. 2020

ChemCatChem

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Selective functionalization of ubiquitous CÀ H bonds of molecules would provide novel retrosynthetic insights and powerful tools for the rapid construction of molecular complexity. In this context, Cp*Ir(III) complexes have exhibited versatile reactivity towards the selective conversion of CÀ H bonds, with key features that include the use of readily transformable raw materials, great selectivity (chemo-, stereo-and regio-), high efficiency, mild reaction conditions and they enable late-stage modification of complex molecules. Recently, Cp*Ir(III) catalysis has achieved a broad range of reactions such as multiple dehydrogenations and stereoselective CÀ X bond formations. These advancements are valuable to organometallic chemists and enable the efficient synthesis of functionalized architectures.

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Iridium-Catalyzed ortho-C(sp²)–H Amidation of Benzaldehydes with Organic Azides

Cited by 54 publications

References 52 publications

Aromatic Aminocatalysis

Aromatic Aminocatalysis

Cp*Co(III)‐Catalyzed o‐Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Group Strategy

Recent Development on Cp*Ir(III)‐Catalyzed C−H Bond Functionalization

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Iridium-Catalyzed ortho-C(sp2)–H Amidation of Benzaldehydes with Organic Azides

Cited by 54 publications

References 52 publications

Aromatic Aminocatalysis

Aromatic Aminocatalysis

Cp*Co(III)‐Catalyzed o‐Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Group Strategy

Recent Development on Cp*Ir(III)‐Catalyzed C−H Bond Functionalization

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Iridium-Catalyzed ortho-C(sp²)–H Amidation of Benzaldehydes with Organic Azides