Sodium-iodide-promoted nickel-catalyzed C–N cross-coupling of aryl chlorides and<i>N</i>-nucleophiles under visible-light irradiation

Feng, Yunhui; Luo, Hang; Yu, Fangnian; Liao, Qian; Lin, Luqing

doi:10.1039/d2gc04630j

Cited by 9 publications

(5 citation statements)

References 47 publications

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“…Recently, the same group further realized Single Ni‐metallaphotoredox BHA of inactive aryl chlorides with aromatic and aliphatic amines under blue light irradiation (Scheme 22b) [11a] . The presence of Ni(0) species and sodium iodide as the activator involving halogen exchange was prerequisite to ensure high catalytic efficiency, as comprehensively explained in the reaction mechanism study (Scheme 22c).…”

Section: Single Ni‐metallaphotoredox Bhamentioning

confidence: 98%

Nickel Metallaphotoredox Buchwald–Hartwig Amination Reactions: A Perspective on Irradiation Light Wavelength

Kuai,

Jia,

Chen

et al. 2023

Eur J Org Chem

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The construction of C‐N bonds is considered as the most useful reaction in the synthetic chemistry due to their widespread presence in pharmaceuticals, natural products, etc.. Pd‐catalyzed Buchwald‐Hartwig amination (BHA) has provided the most efficient method to form (hetero)aryl amines but requiring strong base and sophisticated ligands. In comparison, the combination of photocatalysis and nickel chemistry has revolutionized catalytic strategies and is emerging as a quintessence to realize BHAs, termed as Ni‐metallaphotoredox BHA. To pursue a universal protocol, diverse photocatalysts are designed and employed in Ni‐metallaphotoredox BHA, and smoothly promote C‐N bond formations under irradiation of light from ultraviolet to red light respectively. Note that the matching of photocatalyst and light is critical to the success. Therefore, this review mainly focuses on the discussion of Ni‐metallaphotoredox BHAs according to irradiation light’s wavelength, covering ultraviolet, purple, blue, red and white light as well as solar light. We try to find a clue in structure‐photophysical behaviors of photocatalysts under the same or different irradiation light. At last, current limitations and potential trends for advancing Ni‐metallaphotoredox BHAs are highlighted. We deem that it could encourage chemists to continue designing suitable photocatalyst for C‐N bond formations under sunlight mimicking plants' photosynthesis.

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Section: Single Ni‐metallaphotoredox Bhamentioning

confidence: 98%

Nickel Metallaphotoredox Buchwald–Hartwig Amination Reactions: A Perspective on Irradiation Light Wavelength

Kuai,

Jia,

Chen

et al. 2023

Eur J Org Chem

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“…3 The addition of NaI is reported to facilitate the reaction of aryl chlorides via the halide exchange. 4 Additionally, the ligand designing might also assist in overcoming the low reactivity issue; for example, electron-rich ligands usually perform better in the oxidative addition of aryl chlorides than electron-deficient ligands. 5 The presence of a suitable base makes the transmetalation step more accessible.…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

“…Lin et al reported nickel-catalyzed C–N cross-couplings of aryl chlorides and aryl amines promoted by sodium iodide under visible-light irradiation (455 nm). 4 The light irradiation generated a Ni(I) species via the formation of aryl radicals, with halogen exchange being a critical step in this reaction (Scheme 27 ). Control experiments suggested that the addition of NaI was essential.…”

Section: Buchwald–hartwig Amination Reactionsmentioning

confidence: 99%

Latest Developments on Palladium- and Nickel-Catalyzed Cross-Couplings Using Aryl Chlorides: Suzuki–Miyaura and Buchwald–Hartwig Reactions

Yamada,

Sen

2024

Synthesis

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Palladium- and nickel-catalyzed cross-couplings are powerful methods for constructing C-C and C-N bonds, particularly through Suzuki-Miyaura and Buchwald-Hartwig reactions. Although aryl iodides, bromides, and triflates are the most commonly used substrates, aryl chlorides are less frequently utilized due to their lower reactivity. However, they are appealing because they are readily available and inexpensive. This short review highlights recent developments in Suzuki-Miyaura and Buchwald-Hartwig cross-couplings of aryl chlorides, using both homogeneous and heterogeneous catalysis with palladium and nickel.

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“…Recently, our group has developed a single nickel-catalyzed CÀ N crosscoupling of aryl chlorides/bromides by adding sodium iodide as the activator. [36] In the process, the aryl chlorides can couple with diverse N-nucleophiles with broad functional group tolerance, although the aryl chlorides are limited to the electron-deficient substrates. Various aryl bromides including the electron-rich substrates showcased high reactivity with diverse N-nucleophiles at room temperature.…”

Section: Both Excited Ni II and Ni Iii Complexes For Facile Reductive...mentioning

confidence: 99%

“…Thus, if the ligand exchange is not very fast, the two catalytic pathways might co‐exist during the process of carbon‐heteroatom coupling. Recently, our group has developed a single nickel‐catalyzed C−N cross‐coupling of aryl chlorides/bromides by adding sodium iodide as the activator [36] . In the process, the aryl chlorides can couple with diverse N‐nucleophiles with broad functional group tolerance, although the aryl chlorides are limited to the electron‐deficient substrates.…”

Section: Both Excited Niii and Niiii Complexes For Facile Reductive E...mentioning

confidence: 99%

Recent Advance in Single Nickel Photocatalysis for Carbon‐Heteroatom Bond Formation

2023

Self Cite

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The widely used nickel catalysis for carbon‐heteroatom cross‐coupling reactions often requires high energy to achieve reductive elimination on NiII complexes. To overcome the energy barrier of reductive elimination, the NiII complexes often transform to NiIII facile reductive elimination via single electron transfer in photochemistry. Energy transfer to form the excited‐state NiII complexes is feasible as well for carbon‐heteroatom couplings in nickel catalysis. This Review is focused on the discussion about the variant nickel(II) complexes as the precatalysts to forge diverse carbon‐heteroatom bonds under visible‐light irradiation in the absence of exogenous photocatalysts. Summary of photoactive nickel catalysis aims to promote the development of cheap, abundant metals catalyzed carbon‐heteroatom couplings for efficient preparation of highly valuable chemicals.

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Sodium-iodide-promoted nickel-catalyzed C–N cross-coupling of aryl chlorides andN-nucleophiles under visible-light irradiation

Abstract: Herein, we report visible-light-promoted single nickel catalysis to smoothly achieve various C-N couplings of aryl chlorides/bromides and diverse N-nucleophiles with sodium iodide as the activator. Single nickel catalyst plays two...

Cited by 9 publications

References 47 publications

Nickel Metallaphotoredox Buchwald–Hartwig Amination Reactions: A Perspective on Irradiation Light Wavelength

Nickel Metallaphotoredox Buchwald–Hartwig Amination Reactions: A Perspective on Irradiation Light Wavelength

Latest Developments on Palladium- and Nickel-Catalyzed Cross-Couplings Using Aryl Chlorides: Suzuki–Miyaura and Buchwald–Hartwig Reactions

Recent Advance in Single Nickel Photocatalysis for Carbon‐Heteroatom Bond Formation

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