Boracene-based alkylborate enabled Ni/Ir hybrid catalysis

Sato, Yukiya; Miyamoto, Yusuke; Sumida, Yuto; Hosoya, Takamitsu; Ohmiya, Hirohisa

doi:10.1039/d0ob01610a

Cited by 15 publications

(7 citation statements)

References 39 publications

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“…The distance is about 3 cm between the light source and the irradiation vessel. Quinolinones were synthesized according to procedures described in the previous literature. ,, …”

Section: Methodsmentioning

confidence: 99%

Direct Alkylation of Quinoxalinones with Boracene-Based Alkylborate under Visible Light Irradiation

et al. 2023

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An efficient synthesis of a variety of 3-alkyl quinoxalinones via C–H direct alkylation by photoredox catalysis between quinoxalinones and alkylborates is reported. A range of quinoxalinones was tolerated well. This visible-light photocatalysis reaction allows access to structurally diverse 3-alkyl quinoxalinones in good to excellent yields. The practicality of this protocol was demonstrated by the concise synthesis of a potential bioactive nonpeptide angiotensin II receptor antagonist.

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“…The distance is about 3 cm between the light source and the irradiation vessel. Quinolinones were synthesized according to procedures described in the previous literature. ,, …”

Section: Methodsmentioning

confidence: 99%

Direct Alkylation of Quinoxalinones with Boracene-Based Alkylborate under Visible Light Irradiation

et al. 2023

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“…The same group also presented a variation of the previously discussed nickel catalyzed cross‐coupling reaction, [63] where the addition of an iridium photocatalyst sharply increased the reaction efficiency (Scheme 31). [64] The product yield was found to be higher in many cases and the reaction times were considerably decreased even under the irradiation of a Micro Photochemical Reactor, which has a weaker spectral irradiance in comparison to the most frequently used irradiation sources.…”

Section: Direct Excitation Of Boronate Complexesmentioning

confidence: 99%

Uncovering the Potential of Boronic Acid and Derivatives as Radical Source in Photo(electro)chemical Reactions

et al. 2022

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The chemistry of boron compounds has been profoundly investigated in the last decades, leading to ubiquity in many synthetic applications as well as biologically active molecules. Since the advent of photoredox catalysis, an upsurge in the discovery of suitable radical precursors has been witnessed, and boron is becoming a protagonist in this field. Despite many studies focused on trifluoroborates, the use of boronic acids and esters have received much less attention in this regard. Because of their high oxidation potential, the development of methods to enable their involvement in photocatalyzed reactions is only recent. Nonetheless, this review summarizes novel strategies developed to unlock their role as radical precursors in photochemical reactions and discloses the potential that boronic acids and esters own, when their intrinsic chemical properties are exploited.

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“…Sumida, Hosoya and Ohmiya's group also discovered a more efficient process for tert-alkylative S-M couplings with a boracene-based alkylborate (18.1 and 19.1) (Scheme 18). 21 In the reaction shown in Scheme 17, they used a Kessil lamp as a light source, and the reaction time was 14 h. On the other hand, an upgraded reaction, shown in Scheme 18, employed a photochemical microreactor (weak light source) and shorter reaction time (1 h). The key to the success of this reaction is to use an Ir-photocatalyst (19).…”

Section: N Tsuchiya Et Almentioning

confidence: 99%

Tertiary Alkylative Suzuki–Miyaura Couplings

2022

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The Suzuki-Miyaura coupling is extremely useful to construct Csp2-Csp2 carbon bonds. On the other hand, Csp2-Csp3 coupling reactions are do not work well, and tert-alkylative Suzuki-Miyaura coupling is particularly challenging due to problematic oxidative addition and beta-hydride elimination side reactions. In this short review, we will introduce recent examples of tert-alkylative Suzuki-Miyaura couplings with tert-alkyl electrophiles or -boron reagents. The review will mainly focus on catalyst and product structures and the proposed mechanisms .

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Boracene-based alkylborate enabled Ni/Ir hybrid catalysis

Abstract: The boracene-based alkylborate enabled visible light-mediated metallaphotoredox catalysis. The directly excited borate was easily oxidatively quenched by the excited Ir photoredox catalyst. The Ni/Ir hybrid catalysis afforded the products under...

Cited by 15 publications

References 39 publications

Direct Alkylation of Quinoxalinones with Boracene-Based Alkylborate under Visible Light Irradiation

Direct Alkylation of Quinoxalinones with Boracene-Based Alkylborate under Visible Light Irradiation

Uncovering the Potential of Boronic Acid and Derivatives as Radical Source in Photo(electro)chemical Reactions

Tertiary Alkylative Suzuki–Miyaura Couplings

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