Visible-Light-Induced Nickel-Catalyzed Cross-Coupling of Aryl Bromides with Nitriles

Gao, Jie; He, Xian-Chen; Liu, Yan-Ling; Li, Ke-Rong; Guan, Jian-Ping; Chen, Hong-Bin; Xiang, Hao-Yue; Chen, Kai; Yang, Hua

doi:10.1021/acs.orglett.3c03458

Cited by 5 publications

(3 citation statements)

References 29 publications

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“…Based on the experimental results and previous reports, − a plausible reaction mechanism is proposed as shown in Scheme . Initially, (dtbbpy)Ni II CO 3 I was reduced by photoexcited HE* to deliver the real catalyst species (dtbbpy)Ni I X II .…”

Section: Resultsmentioning

confidence: 84%

“…Pioneered by MacMillan et al, Martin et al, and Yuan et al, the field of photoredox/nickel catalysis has been extensively explored for the facile generation of alkyl radical species by using alkyl halide as the sole electrophilic reagent. Notably, Hantzsch ester was frequently employed to facilitate the single electron transfer (SET) or ligand–metal charge transfer (LMCT) progress to generate reactive Ni I species . Thereafter, single-electron reduction of alkyl halide by low-valent nickel species triggered the subsequent transformations to accomplish a range of alkylation transformations .…”

Section: Introductionmentioning

confidence: 99%

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Visible Light-Induced, Nickel-Catalyzed Late-Stage 4-Alkylation of Hantzsch Esters with Alkyl Bromide

Liu,

He,

Gao

et al. 2024

J. Org. Chem.

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Herein, visible light-induced, nickel-catalyzed direct functionalization of the Hantzsch esters (HEs) with readily accessible alkyl bromides has been successfully achieved by taking advantage of HE as the reductant and substrate through an aromatization-dearomatization process. In this strategy, the single electron reduction of alkyl bromides by reactive Ni(I) species is essential for the success of this late-stage transformation. A wide range of 4-alkyl-1,4-dihydropyridines were rapidly assembled in moderate to good yields under mild conditions, rendering this photoinduced approach attractive for synthetic and medicinal chemistry.

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Section: Resultsmentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Visible Light-Induced, Nickel-Catalyzed Late-Stage 4-Alkylation of Hantzsch Esters with Alkyl Bromide

Liu,

He,

Gao

et al. 2024

J. Org. Chem.

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“…On the basis of the above experimental results and other reports, , a plausible reaction pathway is depicted as shown in Scheme . Upon irradiation by visible light, the photocatalyst was photoexcited into the excited state *[Ir(dF(CF 3 )ppy) 2 (dtbbpy)][PF 6 ].…”

mentioning

confidence: 99%

Photoredox/Nickel Dual Catalysis-Enabled Aryl Formylation with 2,2-Dimethoxy-N,N-dimethylethan-1-amine as CO Source

Gao,

He,

Liu

et al. 2024

Org. Lett.

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Herein, a dual photoredox/nickel catalyzed formylation of aryl bromide with commercially available 2,2-dimethoxy-N,N-dimethylethan-1-amine as an effective CO source has been successfully achieved, delivering a series of aromatic aldehydes in moderate to good yields. Compared with the traditional reductive carbonylation process, this newly designed synthetic protocol provides a straightforward toolbox to access aromatic aldehydes, obviating the use of carbon monoxide and stoichiometric reductants. Finally, the utility of this direct formylation reaction was demonstrated in the pharmaceutical analogue synthesis.

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Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides

Li,

He,

Gao

et al. 2024

J. Org. Chem.

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Nickel/photoredox catalysis has emerged as a powerful platform for exploring nontraditional and challenging crosscouplings. Herein, a metallaphotoredox catalytic protocol has been developed on the basis of a tertiary amine-ligated boryl radicalinduced halogen atom transfer process under blue-light irradiation. A wide variety of aryl and heteroaryl bromides featuring different functional groups and pharmaceutical moieties were facilely coupled to rapidly install C(sp 3 )-enriched aromatic scaffolds. The compatibility of Lewis base-ligated borane with nickel catalysis was well exemplified to extend the chemical space for Ni-catalyzed cross-electrophile coupling.

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Visible-Light-Induced Nickel-Catalyzed Cross-Coupling of Aryl Bromides with Nitriles

Cited by 5 publications

References 29 publications

Visible Light-Induced, Nickel-Catalyzed Late-Stage 4-Alkylation of Hantzsch Esters with Alkyl Bromide

Visible Light-Induced, Nickel-Catalyzed Late-Stage 4-Alkylation of Hantzsch Esters with Alkyl Bromide

Photoredox/Nickel Dual Catalysis-Enabled Aryl Formylation with 2,2-Dimethoxy-N,N-dimethylethan-1-amine as CO Source

Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides

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