Rhodium(III)‐Catalyzed Direct C−H Alkylation of Ferrocenes with Diazo Compounds under Weakly Coordinating Approach

Zhang, Lulu; Jiakai, Zhao; Mou, Qi; Teng, Dawei; Meng, Xiangtai; Sun, Bo

doi:10.1002/adsc.201901193

Cited by 17 publications

(9 citation statements)

References 77 publications

(23 reference statements)

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“…Ferrocenyl amides 184 reacted well in 1,2-dichloroethane with acceptor/acceptor diazo compounds, that is, dimethyl diazomalonate and its analogs, to give the target products 185 (58–86%) (eqn (40)). 235 However, the donor/acceptor diazo compound Ph(CN 2 )CO 2 Me and acceptor/acceptor diazo compound MeCO(CN 2 )CO 2 Et could not undergo the same type of reaction. With [Cp*RhCl 2 ] 2 /NaOAc as the catalyst system C–H functionalization of aryl C(sp 2 )–H bond with 4-diazoisochroman-3-imines enabled the synthesis of tetracyclic isochromeno[3,4- c ]isoquinoline derivatives.…”

Section: Carbene Insertion To Aryl C(sp2)–h Bondsmentioning

confidence: 99%

Recent advances in transition-metal-catalyzed carbene insertion to C–H bonds

Huang

et al. 2022

Chem. Soc. Rev.

172

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Section: Carbene Insertion To Aryl C(sp2)–h Bondsmentioning

confidence: 99%

Recent advances in transition-metal-catalyzed carbene insertion to C–H bonds

Huang

et al. 2022

Chem. Soc. Rev.

172

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“…Under the standard conditions, a wide range of ferrocenes are tested and obtained corresponding monoalkylated products in good yields (Scheme 30). [42] …”

Section: C−h Alkylation With Carbene Precursorsmentioning

confidence: 99%

Co(III), Rh(III) & Ir(III)‐Catalyzed Direct C−H Alkylation/Alkenylation/Arylation with Carbene Precursors

Nunewar

Kumar

Talakola

et al. 2021

Chemistry An Asian Journal

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Metal carbenes play a pivotal role in transition‐metal‐catalyzed synthetic transfer reactions. The metal carbene is generated either from a diazo compound through facile extrusion of N2 with a metal catalyst or in situ generated from other sources like triazoles, pyriodotriazoles, sulfoxonium ylides and iodonium‐ylide. On the other hand, Co(III), Rh(III) & Ir(III)‐catalyzed C−H functionalizations have been well established as a key synthetic step to enable the construction of various synthetic transformations. Interestingly, in recent years, merging of these two concepts C−H activation and carbene migratory insertion gained much attention, in particular group 9 metal‐catalyzed arene C−H functionalizations with carbene precursors via carbene migratory insertion. In this review, we summarize recent advances in Co(III), Rh(III) & Ir(III)‐catalyzed direct C−H alkylation/alkenylation/arylation with carbene precursors and also discuss key synthetic intermediates within the catalytic cycles.

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“…Transition-metal-catalysed C-H activation/annulation with various coupling partners has been developed as a powerful and effective tool to afford diverse carbo-and heterocycles, 1 wherein diverse coupling partners, such as alkenes, 2 alkynes, 3 allenes, 4 diazo compounds 5 and sulfoxonium ylides, 6 have been widely developed as synthons. Very recently, propargyl alcohols have attracted considerable attention for a variety of cyclization reactions, as they exhibit excellent regio-and chemoselective migratory insertion into cyclometallated chelates via weak complexation.…”

Section: Introductionmentioning

confidence: 99%