Selective 1,4-arylsulfonation of 1,3-enynes <i>via</i> photoredox/nickel dual catalysis

Li, Chao; Hu, Duo-Duo; Jin, Ruo-Xing; Wu, Bingbing; Wang, Chengyu; Ke, Zhuofeng; Wang, Xisheng

doi:10.1039/d1qo01653a

Cited by 21 publications

(10 citation statements)

References 86 publications

(3 reference statements)

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“…As disclosed in recent studies, they generally led to poor yields, including our stereoconvergent allenylation reaction (20-23) 50,[53][54][55] . Aliphatic aldehydes, substituted with diverse primary or secondary alkyl chains, participated efficiently in this 1,4functionalization of 1,3-enynes (24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39). However, moderate diastereoselectivities (5:1 dr to 10:1 dr) were generally observed in the cases of primary aliphatic aldehydes (24)(25)(26)(27)(28)(29), probably resulting from the reduced steric hindrance in comparison with secondary alkyl aldehydes (30)(31)(32)(33)(34)(35)(36)(37)(38)(39).…”

Section: Substrate Scopementioning

confidence: 99%

“…1a) 3 . On the other hand, the radical 1,4-functionalization of 1,3-enynes via allenyl or propargylic radicals has attracted much attention recently [20][21][22][23][24][25][26][27][28][29] , but only limited success has been achieved in their asymmetric versions. In 2020, the Bao and Zhang groups 30 , and Liu group 31 independently reported the elegant Cu-catalyzed enantioselective synthesis of chiral allenes via the radical 1,4-dicarbonization of 1,3-enynes.…”

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confidence: 99%

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Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis

et al. 2022

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The merger of photoredox and transition-metal catalysis has evolved as a robust platform in organic synthesis over the past decade. The stereoselective 1,4-functionalization of 1,3-enynes, a prevalent synthon in synthetic chemistry, could afford valuable chiral allene derivatives. However, tremendous efforts have been focused on the ionic reaction pathway. The radical-involved asymmetric 1,4-functionalization of 1,3-enynes remains a prominent challenge. Herein, we describe the asymmetric three-component 1,4-dialkylation of 1,3-enynes via dual photoredox and chromium catalysis to provide chiral allenols. This method features readily available starting materials, broad substrate scope, good functional group compatibility, high regioselectivity, and simultaneous control of axial and central chiralities. Mechanistic studies suggest that this reaction proceeds through a radical-involved redox-neutral pathway.

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Section: Substrate Scopementioning

confidence: 99%

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confidence: 99%

Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis

et al. 2022

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“…Surprisingly, a similar strategy was demonstrated by Ke, Wang, and co-workers towards 1,4-aryl sulfonylation of 1,3-enyne 1 using NiCl 2 and Ru(phen) 3 Cl 2 .6H 2 O photocatalysts at room temperature (Scheme 8b). [32] This protocol displayed a broad substrate scope with high catalytic activity and low catalytic loading, affording the desired α-allenyl sulfones 23 in 40-97 % yield.…”

Section: Chemcatchemmentioning

confidence: 96%

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

2022

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The 1,n-enynes are potent scaffolds in organic synthesis, providing a state-of-the-art approach for synthesizing various acyclic and carbo-and heterocyclic compounds. Radical cascade cyclization and CÀ H functionalization of 1,n-enynes have gained immense attention in the synthetic community. Significant advancement in this field has been developed over the years, employing harsh and expensive metal catalysts usually associated with intense product purification and unwanted side-products. In this context, the advent of visible light photocatalysis as a mild and efficient approach in the area of 1,nenynes is a welcome step. Herein, we provide an exclusive overview of the recent developments in visible light-assisted manipulation of 1,n-enynes. We have classified the review into 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, and 1,8-enynes, as well as dienyne, and enediyne-based reactions.

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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: 99%

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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Selective 1,4-arylsulfonation of 1,3-enynes via photoredox/nickel dual catalysis

Abstract: A photoredox/nickel-catalyzed selective 1,4-arylsulfonation of 1,3-enynes to access structurally diverse sulfone-containing allenes has been established. This radical cascade transformation featured with easy manipulation, mild conditions, low catalyst loading, broad substrate...

Cited by 21 publications

References 86 publications

Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis

Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

Allenyl Radicals in Organic Synthesis: Challenges and Recent Advances

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