Visible Light-Mediated Ullmann-Type C–N Coupling Reactions of Carbazole Derivatives and Aryl Iodides

Yoo, Woo‐Jin; Tsukamoto, Tatsuhiro; Kobayashi, Shū

doi:10.1021/acs.orglett.5b01645

Cited by 97 publications

(66 citation statements)

References 62 publications

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“…43 Recently, Weaver et al studied the important relationship between catalyst structure and cis/trans isomerization of alkenes via energy transfer, 52 but energy transfer between metals is particularly challenging given the lack of systems thought to operate by this mechanism and the difficulty in studying catalytic intermediates that may be transient in nature. 53 …”

Section: Photoredox/nickel Dual Catalysismentioning

confidence: 99%

Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development

et al. 2017

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Photoredox catalysis has experienced a revitalized interest from the synthesis community during the past decade. For example, photoredox/Ni dual catalysis protocols have been developed to overcome several inherent limitations of palladium-catalyzed cross-couplings by invoking a single-electron transmetalation pathway. This Perspective highlights advances made by our laboratory since the inception of the photoredox/Ni cross-coupling of benzyltrifluoroborates with aryl bromides. In addition to broadening the scope of trifluoroborate coupling partners, research using readily oxidized hypervalent silicates as radical precursors that demonstrate functional group compatibility is highlighted. The pursuit of electrophilic coupling partners beyond (hetero)aryl bromides has also led to the incorporation of several new classes of C(sp2)-hybridized substrates into light-mediated cross-coupling. Advances to expand the radical toolbox by utilizing feedstock chemicals (e.g., aldehydes) to access radicals that were previously inaccessible from trifluoroborates and silicates are also emphasized. Additionally, several organic photocatalysts have been investigated as replacements for their expensive iridium- and ruthenium-based counterparts. Lastly, the net C–H functionalization of the radical partner in an effort to improve atom economy is presented. An underlying theme in all of these studies is the value of generating radicals in a catalytic manner, rather than stoichiometrically.

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Section: Photoredox/nickel Dual Catalysismentioning

confidence: 99%

Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development

et al. 2017

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“…However,v isible-light excitation of Ni I -amido 10 should produce along-lived and highly reducing excited *Ni I -amido species 12. [15] Subsequent SET reduction of aryl iodides and bromides by *Ni I -amido species 12 will give an ionic Ni II complex 13 together with an aryl radical. We recognized here that the aminese lectronic properties will have as trong influence on the efficiency of the excitation of 10,the resulting lifetime of 12,and the rate at which 13 reacts with the aryl radical.…”

Section: Angewandte Chemiementioning

confidence: 99%

Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross‐Coupling of Primary Aryl Amines with Aryl Halides

et al. 2016

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A visible-light-promoted iridium photoredox and nickel dual-catalyzed cross-coupling procedure for the formation C-N bonds has been developed. With this method, various aryl amines were chemoselectively cross-coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C-N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir-photoredox/Ni dual-catalyzed procedure very mild and operationally simple.

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“…In recent years, photocatalysis [7] hasb een identifieda sa ni ncreasingly powerful approacht owards variouss ustainable organic syntheses, [8] such as CÀNb ond formations extensively elaborated by Fu, [9] MacMillan, [10] and Kobayashi. [11] Thus, photoredox CÀHf unctionalizations provedv iable,a lthough predominantly relying on precious transition metals,s uch as rhodium,p alladium, and ruthenium complexes. [12] In contrast, we have very recently devised photoinduced CÀHa rylationsa nd chalcogenations by less toxic base metal catalysts (Figure 1a).…”

mentioning

confidence: 99%

Photoinduced Heterogeneous C−H Arylation by a Reusable Hybrid Copper Catalyst

Choi

Müller

Lole

et al. 2020

Chemistry A European J

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Heterogeneous copper catalysis enabled photoinduced C−H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step‐economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.

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Visible Light-Mediated Ullmann-Type C–N Coupling Reactions of Carbazole Derivatives and Aryl Iodides

Abstract: The combined use of an iridium-based photocatalyst and a copper salt under blue light emitting diode irradiation enables the Ullmann-type C-N cross-coupling reaction between carbazole derivatives and aryl iodides to proceed under mild conditions.

Cited by 97 publications

References 62 publications

Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development

Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development

Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross‐Coupling of Primary Aryl Amines with Aryl Halides

Photoinduced Heterogeneous C−H Arylation by a Reusable Hybrid Copper Catalyst

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