Cp*Co(III)-Catalyzed C–H Functionalization Cascade of <i>N</i>-Methoxyamides with Alkynedione for the Synthesis of Indolizidines

Chavan, Lahu N.; Gollapelli, Krishna Kumar; Chegondi, Rambabu; Pawar, Amit B.

doi:10.1021/acs.orglett.7b00904

Cited by 61 publications

(15 citation statements)

References 78 publications

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“…In 2017, the team of Pawar reported the synthesis of indolizidine scaffolds by N ‐methoxyamide‐directed, Cp*Co(III)‐catalyzed ortho ‐C–H activation of aromatic amides (Scheme ) . N ‐Methoxybenzamides and an alkynedione were used as substrates, Cp*Co(CO)I 2 as catalyst, NaOAc as additive, TFE as solvent, and the reaction could be completed under an argon atmosphere at 120 °C for 14 h. The reaction provides a good yield, and it has good functional group applicability.…”

Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning

confidence: 99%

C–H Functionalization of Aromatic Amides

et al. 2020

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Since the beginning of the 21st century, significant progress has been made in transition metal‐catalyzed C–H functionalization of aromatic amides. The achievements in this field have mainly focused on ortho (proximal) functionalization, there have been far fewer reports on remote C–H functionalization, and para‐ and meta‐selective functionalizations remain a major challenge. Interestingly, there are few related comments in this field. In a few published cases, the scope of the report is relatively narrow, either to comment on the functionalization of a specific directing group or to summarize the functionalization of a specific reaction site. Herein, for the first time, we have comprehensively summarized the C–H functionalization of aromatic amides. This review is divided into three parts: ortho‐, para‐ and meta‐C–H functionalization of aromatic amides, and is subdivided according to the type of catalyst. The directing groups, reaction types, conditions, mechanism and applications of the corresponding reactions are discussed in detail.

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Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning

confidence: 99%

C–H Functionalization of Aromatic Amides

et al. 2020

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“…There are some excellent examples in which the nitrogen present in the substrate has been incorporated in the product through a domino process . In this context, Pawar and co‐workers reported the Cp*Co III ‐catalyzed C−H functionalization/nucleophilic addition process for the synthesis of indolizines 40 . Their protocol is highly atom‐economical since it allows the formation of one C−C and two C−N bond in a one‐pot process.…”

Section: Heterocycle Synthesis Through Cascade C−m→c−c→c−n Bond Formamentioning

confidence: 99%

Transition Metal Promoted Cascade Heterocycle Synthesis through C−H Functionalization

Baccalini

Faita

Zanoni

et al. 2020

Chemistry A European J

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Sequential,d omino and tandem reactions could be defined as as equence of synthetic transformationst hat occur one after the other,i nt he same reaction flask. This Review highlights recent advances at the overlap of two worlds:t ransition-metal mediated CÀHa ctivation as at rigger of cascade reaction, for the heterocycles synthesis. To shed some light on this intricate "middle-earth",f ocus was put on the reactionm echanismr ather than the typeo f metal or the chronologicalo rder of the reaction. The aim is to separate, and then highlight, the true domino reactions initiatedb yC ÀHa ctivation, compared to other examples of CÀHf unctionalization for heterocycle syntheses.

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“…In 2017, Pawar and co-workers were able to prepare indolizidines 43 diastereoselectively by reacting N -methoxybenzamides 41 with alkynedione 42 ( Scheme 16 ). 32 To achieve this transformation, the reaction is proposed to proceed through intermediate XVIII , which would be formed after reductive elimination of XVII . The Co(I) species released would be reoxidized to Co(III) with the aid of the N–OCH 3 group that would act as an internal oxidant: Cp*Co(I) is oxidatively added to the N–O bond, forming a Cp*Co(III) species that undergoes proto-demetalation, releasing the active catalytic species alongside the product.…”

Section: Alkynes As Coupling Partners Under Cp*co(iii) Catalysismentioning

confidence: 99%

Cp*Co(III)-Catalyzed C–H Hydroarylation of Alkynes and Alkenes and Beyond: A Versatile Synthetic Tool

2020

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The use of earth-abundant first-row transition metals, such as cobalt, in C–H activation reactions for the construction and functionalization of a wide variety of structures has become a central topic in synthetic chemistry over the last few years. In this context, the emergence of cobalt catalysts bearing pentamethylcyclopentadienyl ligands (Cp*) has had a major impact on the development of synthetic methodologies. Cp*Co(III) complexes have been proven to possess unique reactivity compared, for example, to their Rh(III) counterparts, obtaining improved chemo- or regioselectivities, as well as yielding new reactivities. This perspective is focused on recent advances on the alkylation and alkenylation reactions of (hetero)arenes with alkenes and alkynes under Cp*Co(III) catalysis.

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Cp*Co(III)-Catalyzed C–H Functionalization Cascade of N-Methoxyamides with Alkynedione for the Synthesis of Indolizidines

Cited by 61 publications

References 78 publications

C–H Functionalization of Aromatic Amides

C–H Functionalization of Aromatic Amides

Transition Metal Promoted Cascade Heterocycle Synthesis through C−H Functionalization

Cp*Co(III)-Catalyzed C–H Hydroarylation of Alkynes and Alkenes and Beyond: A Versatile Synthetic Tool

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