Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification

Liang, Yu‐Feng; Steinbock, Ralf; Münch, Annika; Ackermann, Lutz

doi:10.1002/anie.201801111

Cited by 36 publications

(10 citation statements)

References 72 publications

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“…In 2018, Ackermann and colleagues reported on a Mn-catalyzed, carbonylative alkyne annulation protocol with excellent regioselectivity, which can find application in late-stage diversification of a variety of molecules with pharmaceutical interest and natural products such as amino acids, alkaloids, carbohydrates, and steroids [85]. Even though this protocol does not comprise a C-H activation, it utilizes a hydrazone as a TDG and, therefore, is presented herein as it comprises an example for future developments in TDG-assisted C-H activation.…”

Section: Annulations Via C(sp 2 )-H Bond Activationmentioning

confidence: 99%

Traceless Directing Groups in Sustainable Metal-Catalyzed C–H Activation

et al. 2021

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Sustainable transformations towards the production of valuable chemicals constantly attract interest, both in terms of academic and applied research. C–H activation has long been scrutinized in this regard, given that it offers a straightforward pathway to prepare compounds of great significance. In this context, directing groups (DG) have paved the way for chemical transformations that had not been achievable using traditional reactions. Few steps, high yields, selectivity and activation of inert substrates are some of the invaluable assets of directed catalysis. Additionally, the employment of traceless directing groups (TDG) greatly improves and simplifies this strategy, enabling the realization of multi-step reactions in one-pot, cascade procedures. Cheap, abundant, readily available transition metal salts and complexes can catalyze a plethora of reactions employing TDGs, usually under low catalyst loadings—rarely under stoichiometric amounts, leading in greater atom economy and milder conditions with increased yields and step-economy. This review article summarizes all the work done on TDG-assisted catalysis with manganese, iron, cobalt, nickel, or copper catalysts, and discusses the structure-activity relationships observed, by presenting the catalytic pathways and range of transformations reported thus far.

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Section: Annulations Via C(sp 2 )-H Bond Activationmentioning

confidence: 99%

Traceless Directing Groups in Sustainable Metal-Catalyzed C–H Activation

et al. 2021

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“…Even though previous methods described above give possibilities for the synthesis of C-3-substituted derivatives, further functionalization can be achieved through the method reported by Ackermann et al [ 71 ]. Starting from 2-pyridylhydrazone 49 and alkyne 50a,b , manganese-catalyzed carbonylative annulations yielding compounds 36 and 51 were carried out ( Scheme 18 ).…”

Section: Synthesis Of Functionalized and Heteroatom Containing Kyna Derivativesmentioning

confidence: 99%

KYNA Derivatives with Modified Skeleton; Hydroxyquinolines with Potential Neuroprotective Effect

Lőrinczi

Szatmári

2021

IJMS

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Kynurenic acid (KYNA) is an endogenous neuroprotective agent of increasing importance. Several derivatives have already been synthesized, bearing an abundance of functional groups attached to the main skeleton in different positions. Several of these compounds have already been tested in biological evaluations, with several of them targeting the same receptors and biological effects as KYNA. However, these modified compounds build upon the unmodified KYNA skeleton leaving a possible route for the synthesis of new, potentially neuroprotective derivatives with heteroatom-containing ring systems. The aim of this review is to summarize the syntheses of KYNA derivatives with altered skeletons and to pinpoint an appealing transformation for future medicinal lead molecules.

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“…Various ketazine directed C–H activation reactions are previously reported . In our concern, azine and dibenzoylhydrazine could be one of the best directing groups for the synthesis of isoquinolines and isoquinolinones respectively using C–H activation strategy.…”

Section: Introductionmentioning

confidence: 98%

Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media

2019

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Herein, we report an atom‐efficient, rapid, green, and sustainable approach to synthesize isoquinolines and isoquinolinones using a homogeneous recyclable ruthenium catalyst in PEG Media assisted by microwave energy. Dibenzoylhydrazine was used for C–H/N–N activation reactions for the first time in combination with ketazine as oxidizing directing groups for annulation reactions with internal alkynes. The developed protocol is environmentally benign due to significantly shortened times with an easy extraction method, higher atom economy, external oxidant and silver or antimony salt free conditions, applicability to a gram scale synthesis, use of biodegradable solvent and wide substrate scope with higher product yields. Moreover, it is worth noting that the established methodology allowed reuse of the catalytic system for up to five successive runs with minimal loss in activity.

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Manganese‐Catalyzed Carbonylative Annulations for Redox‐Neutral Late‐Stage Diversification

Cited by 36 publications

References 72 publications

Traceless Directing Groups in Sustainable Metal-Catalyzed C–H Activation

Traceless Directing Groups in Sustainable Metal-Catalyzed C–H Activation

KYNA Derivatives with Modified Skeleton; Hydroxyquinolines with Potential Neuroprotective Effect

Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media

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