Visible-light-induced, autopromoted nickel-catalyzed three-component arylsulfonation of 1,3-enynes and mechanistic insights

Hu, Duo-Duo; Gao, Qian; Dai, Jing-Cheng; Cui, Ru; Li, Yuanming; Zhou, Xiaoguo; Bian, Kang‐Jie; Wu, Bingbing; Zhang, Kaifan; Wang, Xisheng; Li, Yan

doi:10.1007/s11426-021-1193-5

Cited by 22 publications

(6 citation statements)

References 55 publications

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“…Recently, Li and co‐workers developed the similar arylsulfonation of 1,3‐enynes under cooperative photo/nickel catalysis (Scheme 18). [33] Compared with Lu, [30] Li [31] and Wang's work, [32] additional photocatalyst was obviated. This light induced nickel catalysis was autopromoted by the allene product as a co‐ligand in the photoactive excited Ni I species for the ligand‐to‐metal charge transfer (LMCT) process.…”

Section: Metallaphotoredox Catalyzed Reactions Involving Allenyl Radi...mentioning

confidence: 98%

Allenyl Radicals in Organic Synthesis: Challenges and Recent Advances

Zhang

2022

Eur J Org Chem

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Allenyl radicals are rarely employed as intermediates for the synthesis of allenes probably owe to the lack of convenient methods for their generation and the high reactivity of short‐lived allenyl radicals. However, strategies take advantage of allenyl radicals are considered as a significant complement to reactions which couldn't proceed via an allenyl ionic pathway. As a result, several important methods have been developed in the past decades. Herein, this review is aimed to summarize the recent advance in reactions involving allenyl radicals by highlighting some outstanding challenges and confirming potential areas of improvement, which would offer an inspiration for future studies

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Section: Metallaphotoredox Catalyzed Reactions Involving Allenyl Radi...mentioning

confidence: 98%

Allenyl Radicals in Organic Synthesis: Challenges and Recent Advances

Zhang

2022

Eur J Org Chem

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“…The reaction of 1,3-enynes with sulfonyl hydrazides and I 2 in the presence of tert -butyl hydroperoxide (TBHP) at room temperature gave the allenyl iodide products in satisfactory yields with excellent regioselectivity and good functional group tolerance. In 2022, Li and Wang’s group disclosed a visible-light-induced and Ni-catalyzed 1,4-arylsulfonation of 2-methyl-1,3-enynes to synthesize compounds 19 ( Scheme 20 ) [ 52 ].…”

Section: 14-difunctionalization Reactionsmentioning

confidence: 99%

Remote Radical 1,3-, 1,4-, 1,5-, 1,6- and 1,7-Difunctionalization Reactions

Zhang

2023

Molecules

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Radical transformations are powerful in organic synthesis for the construction of molecular scaffolds and introduction of functional groups. In radical difunctionalization reactions, the radicals in the first functionalized intermediates can be relocated through resonance, hydrogen atom or group transfer, and ring opening. The resulting radical intermediates can undertake the following paths for the second functionalization: (1) couple with other radical groups, (2) oxidize to cations and then react with nucleophiles, (3) reduce to anions and then react with electrophiles, (4) couple with metal-complexes. The rearrangements of radicals provide the opportunity for the synthesis of 1,3-, 1,4-, 1,5-, 1,6-, and 1,7-difunctionalization products. Multiple ways to initiate the radical reaction coupling with intermediate radical rearrangements make the radical reactions good for difunctionalization at the remote positions. These reactions offer the advantages of synthetic efficiency, operation simplicity, and product diversity.

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“…Later, Wang et al further discovered that the nickelcatalyzed 1,4-sulfonylarylation of 1,3-enynes with aryl halides and sulfinate salts could also proceed efficiently in the absence of photocatalyst under the irradiation of purple light (Scheme 22). [49] A wide range of sulfone-containing allenes with various useful functional groups were afforded in moderate to good yields by this simple procedure. Furthermore, a series of mechanistic studies were conducted to probe the mechanism of this process by the authors.…”

Section: Allene Synthesis From 13-enynesmentioning

confidence: 99%

Recent Advances in Nickel‐Catalyzed Synthesis of Allenes: New Insights and Perspectives

et al. 2023

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Allenes are one of the most important functional groups in organic chemistry, featuring unique physical and chemical properties. They are not only the key scaffolds widely present in natural products, pharmaceutical molecules, and advanced functional materials, but also the valuable and versatile building blocks for the construction of various complex and bioactive molecules in organic synthesis. Accordingly, benefiting from the rapid development of transition metal catalysis, numerous remarkable and efficient approaches for the synthesis of allenes from readily available chemicals have been established in the past decades. In this brief review, we focus on the recent advancements in nickel‐catalyzed synthesis of allenes. These transformations are divided into two categories according to the types of reactions and sorted further by starting materials. Moreover, a concise discussion of the limitations and potential areas of improvement in this field is also provided, which would give an inspiration for future study on allene synthesis.

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Visible-light-induced, autopromoted nickel-catalyzed three-component arylsulfonation of 1,3-enynes and mechanistic insights

Cited by 22 publications

References 55 publications

Allenyl Radicals in Organic Synthesis: Challenges and Recent Advances

Allenyl Radicals in Organic Synthesis: Challenges and Recent Advances

Remote Radical 1,3-, 1,4-, 1,5-, 1,6- and 1,7-Difunctionalization Reactions

Recent Advances in Nickel‐Catalyzed Synthesis of Allenes: New Insights and Perspectives

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