Cp*Co(<scp>iii</scp>)-catalysed selective alkylation of C–H bonds of arenes and heteroarenes with α-diazocarbonyl compounds

Ghorai, Jayanta; Chaitanya, Manthena; Anbarasan, Pazhamalai

doi:10.1039/c8ob02111b

Cited by 32 publications

(6 citation statements)

References 51 publications

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“…For C2 or C5 substituted pyrroles the reaction happened at C3 [8c] . The N‐aryl or NH‐free pyrroles afforded a mixture of C2 and C5 substituted compounds (Scheme 1c and d) [9a–c] . In general the reported carbene transfer reactions are limited in their diversity [8f] .…”

Section: Introductionmentioning

confidence: 99%

Blue LED Induced Manganese (I) Catalysed Direct C2−H Activation of Pyrroles with Aryl Diazoesters

2021

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Herein, we have reported a blue LED mediated manganese pentacarbonyl bromide catalysed incorporation of carbene moieties from aryl diazoesters onto 1H-pyrroles via their selective C2À H activation. A manganese metal-carbene has been identified as the active catalyst to facilitate the reaction. Eighteen mono substituted pyrrole derivatives were isolated in good to excellent yields (67!82%) and the disubstituted products were also formed in minor quantities (5 to 8%). HPLC based kinetics study enabled optimization of the reaction. Control experiments, FT-IR, NMR and GC-MS based characterization elucidated the putative reaction mechanism.

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Section: Introductionmentioning

confidence: 99%

Blue LED Induced Manganese (I) Catalysed Direct C2−H Activation of Pyrroles with Aryl Diazoesters

2021

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“…To the best of our knowledge, there are only two reports using either cobalt‐ or rhodium‐based catalysts for directing group‐assisted C−H functionalization reactions with donor/acceptor diazoalkanes, however rapid intramolecular amide formation occurs and prevents isolation of the C−H functionalization product [10] . Furthermore, there is one study on the cobalt‐catalyzed C−H functionalization of 1‐(pyridine‐2‐yl)‐1 H ‐indole and 1‐aryl‐1 H ‐pyrazoles [11] …”

Section: Resultsmentioning

confidence: 99%

Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions

Empel

Jana

Langletz

et al. 2022

Chemistry A European J

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In this combined computational and experimental study, the C−H functionalization of 2‐phenyl pyridine with diazoalkanes was investigated. Initial evaluation by computational methods allowed the evaluation of different metal catalysts and diazoalkanes and their compatibility in this C−H functionalization reaction. With these findings, suitable reaction conditions for the C−H methylation reactions were quickly identified by using highly reactive TMS diazomethane and C−H alkylation reactions with donor/acceptor diazoalkanes, which is applied to a broad scope on alkylation reactions of 2‐aryl pyridines with TMS diazomethane and donor/acceptor diazoalkane (51 examples, up to 98 % yield).

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“…Furthermore, by use of this method as the key transformation, the authors successfully achieved potent anti‐cancer activity 2‐aroylindole derivative in moderate yield (Scheme 11). [24c] …”

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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Cp*Co(iii)-catalysed selective alkylation of C–H bonds of arenes and heteroarenes with α-diazocarbonyl compounds

Abstract: Cp*Co(iii)-catalysed selective alkylation of directed C–H bonds of arenes and heteroarenes has been accomplished employing donor–acceptor carbenes, derived from α-diazocarbonyl compounds.

Cited by 32 publications

References 51 publications

Blue LED Induced Manganese (I) Catalysed Direct C2−H Activation of Pyrroles with Aryl Diazoesters

Blue LED Induced Manganese (I) Catalysed Direct C2−H Activation of Pyrroles with Aryl Diazoesters

Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions

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

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