Synthesis of 1-naphthols <i>via</i> Cp*Co(<scp>iii</scp>)-catalyzed C–H activation and cyclization of sulfoxonium ylides with alkynes

Yu, Yongqi; Wu, Qianlong; Liu, Da; Lin, Ying‐Chu; Tan, Ze; Zhu, Gangguo

doi:10.1039/c9qo00994a

Cited by 43 publications

(17 citation statements)

References 91 publications

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“…Reductive elimination leads to the Co(I) intermediate V, followed by oxidative addition of the metal to the N-O bond and protodemetallation to C8 functionalized quinoline 217, with the concomitant regeneration of the active catalyst (Scheme 17). Another protocol catalyzed by Cp*Co(III) species was reported by Tan and co-workers in 2019, enabling C-H activation and [4 + 2] cyclization of readily available sulfoxonium ylides with alkynes for the synthesis of 1-naphthols [111]. 1-Naphthols are scaffolds widely found in pharmaceuticals and bioactive natural products; therefore, the direct synthesis of these compounds via earth-abundant, cheap, and biocompatible first-row transition metal catalysis is of great interest.…”

Section: Other Tdg-assisted Transformationsmentioning

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: Other Tdg-assisted Transformationsmentioning

confidence: 99%

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

et al. 2021

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“…Alkynes have been subjected to numerous reactions, such as CÀ C coupling, dimerization, annulation and oxidation reactions. [6] Annulations of alkynes have been found to constitute a good overall strategy for synthesizing heterocyclic compounds such as oxazoles, [7] 1-naphthols, [8] α-pyrones, [9] isoindolones, [10] and benzoxazines. [11] However, the annulation of an alkyne is considered to be difficult to carry out without the participation of an external oxidant or transition metal.…”

Section: Electrochemically Enabled Intramolecular Annulations Of Alkynesmentioning

confidence: 99%

Electrochemically Enabled Intramolecular and Intermolecular Annulations of Alkynes

Sun

Liu

et al. 2020

Adv Synth Catal

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Electrosynthesis is recognized as one of the most powerful and sustainable methods in organic chemistry. Recently, electrochemically enabled annulations of carbon‐carbon triple bonds have been successfully achieved, and have broadened prospects for the application of the emerging method with cyclization of alkynes. Thus, herein we outline the recent progress made on electrochemically enabled annulations of alkynes. In addition, an emphasis on the scope, limitations and the mechanisms of these reactions is made in this review.

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“…Similarly, cobalt(III) can also activate C(sp 2 )–H bonds in sulfoxonium ylides 101 , forming cobaltacycles, and undergoing alkyne 102 insertion in a similar catalytic cycle to the aforementioned rhodium variant (Scheme 18b). [ 64 ] Moreover, the cobalt‐catalyzed system functioned under an air atmosphere to access naphthols 103 , and was compatible with both internal and terminal alkynes 102 .…”

Section: Synthesis Of Substituted Naphthols From Sulfur Ylidesmentioning

confidence: 99%

Substituted Naphthols: Preparations, Applications, and Reactions

2020

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Substituted naphthols (SNs) are an important class of chemical compounds present in many natural and synthetic products with biological and pharmaceutical activities. Moreover, the naphthol skeleton has been employed as a starting material for the development of drug molecules and natural products. Thus, different synthetic methods to access naphthol cores have been reported using diverse starting materials and chemical strategies. This review article describes literature on synthetic methodologies of substituted naphthols synthesized from alkynes, sulfur ylides, diazo substrates, alkenes/cyclopropenes, ketones/oxanorbenes/furans, amongst other key reactants.

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Synthesis of 1-naphthols via Cp*Co(iii)-catalyzed C–H activation and cyclization of sulfoxonium ylides with alkynes

Abstract: A highly practical synthesis of 1-naphthols was developed via Cp*Co(iii)-catalyzed C–H activation and cyclization between sulfoxonium ylides and alkynes.

Cited by 43 publications

References 91 publications

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

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

Electrochemically Enabled Intramolecular and Intermolecular Annulations of Alkynes

Substituted Naphthols: Preparations, Applications, and Reactions

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