Transition metal-catalyzed coupling of heterocyclic alkenes<i>via</i>C–H functionalization: recent trends and applications

Kumar, Sundaravel Vivek; Banerjee, Sonbidya; Punniyamurthy, Tharmalingam

doi:10.1039/d0qo00279h

Cited by 81 publications

(16 citation statements)

References 288 publications

(200 reference statements)

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“…Over the past few decades, outstanding progress has been realized in the direct alkenylation transformation of C(sp 2 )-H bonds [95][96][97][98][99][100][101]. However, the related C(sp 3 )-H alkenylation is much less developed due to lower reactivity, poor regioselectivities and the need of noble metal catalysts [50,[102][103][104][105][106].…”

Section: Alkenylationmentioning

confidence: 99%

Photoredox catalysis in nickel-catalyzed C–H functionalization

Mantry¹,

Maayuri²,

Kumar³

et al. 2021

Beilstein J. Org. Chem.

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Catalytic C‒H functionalization has become a powerful strategy in organic synthesis due to the improved atom-, step- and resource economy in comparison with cross-coupling or classical organic functional group transformations. Despite the significant advances in the metal-catalyzed C‒H activations, recent developments in the field of metallaphotoredox catalysis enabled C‒H functionalizations with unique reaction pathways under mild reaction conditions. Given the relative earth-abundance and cost-effective nature, nickel catalysts for photoredox C‒H functionalization have received significant attention. In this review, we highlight the developments in the field of photoredox nickel-catalyzed C‒H functionalization reactions with a range of applications until summer 2021.

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Section: Alkenylationmentioning

confidence: 99%

Photoredox catalysis in nickel-catalyzed C–H functionalization

Mantry¹,

Maayuri²,

Kumar³

et al. 2021

Beilstein J. Org. Chem.

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“…In recent years, transition metal (TM)-catalyzed inert C–H bond functionalization followed by intramolecular annulation has rapidly bloomed as an atom- and step-economical synthetic strategy to construct polycyclic molecular frameworks . Among the TMs exploited in this field, ruthenium is particularly attractive due to its less expensive and more elusive nature.…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of Dihydrophenanthridine and Phenanthridine Derivatives from the Cascade Reactions of o-Arylanilines with Alkynoates through C–H/N–H/C–C Bond Cleavage

Zhang

et al. 2021

J. Org. Chem.

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In this paper, an unprecedented selective synthesis of dihydrophenanthridine and phenanthridine derivatives through the cascade reactions of 2-arylanilines with alkynoates is presented. Mechanistic studies showed that the formation of the dihydrophenanthridine scaffold involves an initial C(sp2)–H alkenylation of 2-arylaniline with alkynoate followed by an intramolecular aza-Michael addition. When this reaction is carried out at elevated temperature, the in situ formed substituted dihydrophenanthridine readily undergoes a retro-Mannich-type reaction to give the corresponding phenanthridine through C–C bond cleavage. Compared with literature methods, this novel protocol has advantages such as easily obtainable substrates with a free amino group, pharmaceutically privileged products, cheap catalysts, and conveniently controllable selectivity.

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“…Oxa- and azabicyclic alkenes, due to their intrinsic reactivity with transition-metal catalysts and special bridged-ring systems, have been widely used in various organic transformations such as ring-opening reactions (Scheme a), hydrofunctionalizations , (Scheme b), cycloadditions , (Scheme c), and C–H activations. , In these related transition-metal-catalyzed C–H activations, oxa- and azabicyclic alkenes always went through two paths assisted by the transition-metal chelation: (1) serving as a common alkene to deliver the coupling product accompanied by ring opening or subsequent elimination (Scheme d) and (2) proceeding by a cascade cyclization with the preinstalled directing group (Scheme e) . The latter path provided a rapid and efficient way to obtain polycyclic heterocycles.…”

mentioning

confidence: 99%

Benzocarbazole Synthesis via Visible-Light-Accelerated Rh(III)-Catalyzed C–H Annulation of Aromatic Amines with Bicyclic Alkenes

et al. 2021

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A visible-light-accelerated Rh(III)-catalyzed C–H annulation of aromatic amines with bicyclic alkenes for the synthesis of benzocarbazole derivatives was developed. In this approach, with the cooperation of rhodium catalysis and visible-light irradiation, various aromatic amines reacted with oxabicyclic alkenes and azabicyclic alkenes smoothly at room temperature, delivering the corresponding bridged oxa or aza tetrahydro benzocarbazoles in good to excellent yields. Moreover, a series of benzo[b]carbazoles were synthesized conveniently through further aromatization in one pot. The potential of this method was demonstrated via directing-group removal, derivatization, a scale-up reaction, and fluorescence investigations.

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Transition metal-catalyzed coupling of heterocyclic alkenesviaC–H functionalization: recent trends and applications

Abstract: Heterocyclic alkenes and their derivatives are an important class of reactive feedstock and valuable synthons. This review highlights the transition-metal-catalyzed coupling of heterocyclic alkenes via a C–H functionalization strategy.

Cited by 81 publications

References 288 publications

Photoredox catalysis in nickel-catalyzed C–H functionalization

Photoredox catalysis in nickel-catalyzed C–H functionalization

Selective Synthesis of Dihydrophenanthridine and Phenanthridine Derivatives from the Cascade Reactions of o-Arylanilines with Alkynoates through C–H/N–H/C–C Bond Cleavage

Benzocarbazole Synthesis via Visible-Light-Accelerated Rh(III)-Catalyzed C–H Annulation of Aromatic Amines with Bicyclic Alkenes

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