Thiocarbonyl-enabled ferrocene C–H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical

Yetra, Santhivardhana Reddy; Shen, Zhongrong; Wang, Hui; Ackermann, Lutz

doi:10.3762/bjoc.14.131

Cited by 47 publications

(24 citation statements)

References 106 publications

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“…由于烯胺酮基团的亲电性, 反应可通过羰基导向的一锅法生成胺化产物后, 在盐酸的作用下继续进行水解-环化反应, 生成喹诺酮类产物. 朱进课题组 [98] 、Ackermann 课题组 [99] 和牛俊龙课题组 [100] 8-Aminoquinoline-directed nickel-catalyzed C(sp 2 )-H amination and mechanism 2018 年, 谭泽和桂清文课题组 [111] 报道了 8-氨基喹啉导向镍催化苯甲酰胺邻位碳氢键胺化反应(Scheme 47, a). 该反应采用廉价的叠氮化钠作为胺化试剂, 可以兼容较多官能团, 如烯基、硝基、酯基等.…”

Section: 以羟胺及其衍生物为胺化试剂unclassified

Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination

Feng¹,

Shi²

2021

Chinese Journal of Organic Chemistry

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Nitrogen-containing organic compounds are ubiquitous in natural products, drug molecules and organic intermediates. Therefore, the introduction of nitrogenous functional groups into organic compounds is of great significance. Despite transition metalcatalyzed C-N coupling reaction provided an effcient strategy to access these ntrogen-containing compounds, extra steps are generally required to obtain the pre-functionalized starting materials. Recently, transi-tionmetalcatalyzed C-H amination has emerged as a more atom-and step-economical strategy to construct C-N bonds. Compared to the noble metals (e.g. palladium and rhodium), base metal catalysts, such as copper, cobalt and nickel, have attracted dramatic attentions, due to their earth abundance, cost effectiveness, and unique catalytic activities. Herein, the recent advances in copper-, cobalt-and nickel-catalyzed C-H amination reactions assisted by directing groups were summmarized according to the types of base metals, C-H bonds, and amination reagents with an emphasis on the discussion of various amination reagents and their application. Finally, the limitations and development trend of this research field are analyzed and prospected.

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Section: 以羟胺及其衍生物为胺化试剂unclassified

Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination

Feng¹,

Shi²

2021

Chinese Journal of Organic Chemistry

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“…[58] Im darauffolgenden Jahr entwarf die Gruppe von Shi einen neuen chiralen, einfach-geschützten Aminosäure (MPAA)-Liganden, um die Amidierung von Ferrocenthioamiden 73 enantioselektiv durchzuführen (Schema 22). Die Reaktion zeigte eine beachtliche Toleranz fürf unktionelle Gruppen und stellte ein präzedenzloses Beispiel der enantioselektiven C(sp 3 )-H-Aktivierung durch 3d-Übergangsmetallkatalysedar.…”

Section: Cobalt(iii)-katalyseunclassified

Enantioselektive C‐H‐Aktivierung mit natürlich vorkommenden 3d‐Übergangsmetallen

et al. 2019

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Molekulare Synthese basiert größtenteils auf zeit‐ und arbeitsintensiven Präfunktionalisierungsstrategien. Demgegenüber bietet die C‐H‐Aktivierung ein leistungsstarkes Hilfsmittel, das ohne lange Synthesen präfunktionalisierter Substrate auskommt und großes Potenzial für z. B. die Wirkstoffentwicklung, die pharmazeutische Industrie, die Materialwissenschaften und die Synthese von Pflanzenschutzmitteln hat. Die enantioselektive Funktionalisierung omnipräsenter C‐H‐Bindungen hat sich zu einer etablierten Methode für die stufen‐ und atomökonomische Synthese komplexer chiraler Moleküle entwickelt. Allerdings ist dieses rasant wachsende Feld größtenteils durch die Verwendung edler Übergangsmetalle geprägt, mit besonderer Präsenz toxischer Palladium‐, Iridium‐ und Rhodiumkatalysatoren. Trotz bedeutender Errungenschaften befindet sich die asymmetrische C‐H‐Aktivierung unter Verwendung kostengünstiger und nachhaltiger 3d‐Metalle noch im Anfangsstadium. In diesem Kurzaufsatz diskutieren wir die neuen, herausragenden Fortschritte bei enantioselektiven Transformationen über metallorganische C‐H‐Aktivierungen durch 3d‐Basismetalle bis April 2019.

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“…Recently, transition metalcatalyzed CÀ H functionalization has emerged as the most straightforward and efficient method for the derivatization of ferrocenes via the CÀ C and CÀ Het bonds formation. [4] Despite great achievements for establishing the CÀ Het bonds (CÀ N, S, Se, Te, Si, Ge, B) of ferrocenes have been made, [5][6][7][8] the direct CÀ O formation of ferrocenes remains a noteworthy challenge because of the sensitivity of the phenol analogue hydroxyferrocene [9] or the tendency of oxygen electrophiles. [10] In recent years, cobalt-catalyzed direct CÀ H functionalization have attracted considerable attention because of its versatile reactivity and unique selectivity.…”

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Cobalt‐Catalyzed C−H Alkoxylation of Ferrocenes with Alcohols under Mild Conditions

et al. 2021

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Herein we reported a protocol for synthesis of oxy‐substituted ferrocenes via cobalt‐catalyzed direct C−H alkoxylation under mild conditions. Notably, alcohol serves as an both alkoxide reagent and a solvent. Various ferrocene amides including estrone‐derived ferrocene amide are compatible with these reaction conditions. Moreover, control experiments suggested that this alkoxylation might undergo a Co(III)/Co(IV)/Co(II) catalytic cycle.

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Thiocarbonyl-enabled ferrocene C–H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical

Cited by 47 publications

References 106 publications

Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination

Recent Advances in Base Metal (Copper, Cobalt and Nickel)-Catalyzed Directed C—H Amination

Enantioselektive C‐H‐Aktivierung mit natürlich vorkommenden 3d‐Übergangsmetallen

Cobalt‐Catalyzed C−H Alkoxylation of Ferrocenes with Alcohols under Mild Conditions

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