Regio- and Diastereoselective Decarboxylative Allylation of <i>N-</i>Aryl α-Amino Acids by Dual Photoredox/Nickel Catalysis

Zheng, Jun; Nopper, Christoph; Bibi, Rifhat; Nikbakht, Ali; Bauer, Felix; Breit, Bernhard

doi:10.1021/acscatal.2c01688

Cited by 8 publications

(6 citation statements)

References 61 publications

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“…On the basis of the above experimental results and previous reports, [22–27] a plausible mechanism was proposed for this transformation (Scheme 5). Firstly, Ir[dF(CF 3 )(ppy)] 2 (dtbbpy)PF 6 is excited by blue light irradiation to form the excited state * [Ir[dF(CF 3 )(ppy)] 2 (dtbbpy)PF 6 ].…”

Section: Resultssupporting

confidence: 71%

Visible‐Light‐Induced Synthesis of γ‐Amino Sulfones from Vinyl Sulfones and Amino Acids

Qian,

Wang,

Guan

et al. 2024

Adv Synth Catal

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A method for the synthesis of γ‐amino sulfones through visible light‐induced oxidative decarboxylation and radical reductive addition is described. Various readily available N‐protected natural amino acids react with aromatic/aliphatic vinyl sulfones to directly produce γ‐amino sulfone derivatives. This reaction is also applicable to α‐N(O)‐acids and other aliphatic carboxylic acids, resulting in the corresponding sulfone derivatives. The method operates without the need for sacrificial reducing agents or additional hydrogen atom donors. The sole by‐product is CO2 released from decarboxylation, rendering the process both atom‐ and step‐economical.

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Section: Resultssupporting

confidence: 71%

Visible‐Light‐Induced Synthesis of γ‐Amino Sulfones from Vinyl Sulfones and Amino Acids

Qian,

Wang,

Guan

et al. 2024

Adv Synth Catal

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“…The product is then generated through subsequent nucleophilic attack from the allyl nickel(I) species (Scheme 12). [39] …”

Section: Photoredox‐catalyzed Decarboxylationmentioning

confidence: 99%

“…The product is then generated through subsequent nucleophilic attack from the allyl nickel(I) species (Scheme 12). [39] In 2021, Messaoudi and co-workers developed an Ir/Cu dual catalytic decarboxylative coupling of anomeric carboxylic acids with terminal alkynes (Scheme 13). [40] For the glucofuranosederived acids, β-alkynylated products were obtained exclusively.…”

Section: Photoredox-catalyzed Decarboxylationmentioning

confidence: 99%

Free Carboxylic Acids: The Trend of Radical Decarboxylative Functionalization

Yao

2023

Eur J Org Chem

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The exceptional versatility of carboxylic acids has been extensively exploited in organic synthesis across several decades. There has been a recent upsurge of radical decarboxylative transformations. The process can be initiated under mild conditions, and the resultant radicals have orthogonal reactivities to closed-shell species, thus providing immense opportu-nities for streamlining novel reactions. The use of free carboxylic acids is the most desirable owing to its high atom and step economy. Aiming to demonstrate the attractiveness of the strategy and to inspire chemists to tackle existing challenges, this review outlines the recent advances on radical decarboxylative functionalization of free carboxylic acids.

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“…Recently, this strategy has been employed to achieve diverse transformations under mild reaction conditions, including dehydrodecarboxylation, amination, conjugate addition, sulfonylation, and deuteration (Scheme a). On the contrary, α-amino acids are known as cheap and readily available synthons and have served as precursors of α-amino alkyl radicals in several photocatalytic reactions via an oxidative decarboxylation process. − …”

mentioning

confidence: 99%

2,2′-Bipyridine-Enabled Photocatalytic Radical [4+2] Cyclization of N-Aryl-α-amino Acids for Synthesizing Polysubstituted Tetrahydroquinolines

Xiao,

Tian,

Yang

et al. 2024

Org. Lett.

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A facile photocatalytic radical [4+2] cyclization of N-aryl-α-amino acids with various alkenes to access structurally polysubstituted tetrahydroquinolines has been developed. Using a simple bipyridine as a catalyst, different N-aryl-α-amino acids could be utilized as the radical precursors to react with diverse electrophilic alkenes, including exocyclic terminal alkenes, acyclic terminal alkenes, and cycloalkenes, producing 10 types of nitrogencontaining heterocyclic compounds fused in multiple frameworks in generally moderate yields with good diastereoselectivities. Scaleup synthesis and transformations of the products further demonstrated the synthetic application of this protocol. Moreover, a decarboxylative radial pathway via a proton-coupled electron transfer process for illustration of this [4+2] cyclization was proposed on the basis of the control experiments. This process is highlighted by a simple bipyridine photocatalysis, mild reaction conditions, various N-aryl-α-amino acids and alkene materials, and application for the modification of natural products.

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Regio- and Diastereoselective Decarboxylative Allylation of N-Aryl α-Amino Acids by Dual Photoredox/Nickel Catalysis

Cited by 8 publications

References 61 publications

Visible‐Light‐Induced Synthesis of γ‐Amino Sulfones from Vinyl Sulfones and Amino Acids

Visible‐Light‐Induced Synthesis of γ‐Amino Sulfones from Vinyl Sulfones and Amino Acids

Free Carboxylic Acids: The Trend of Radical Decarboxylative Functionalization

2,2′-Bipyridine-Enabled Photocatalytic Radical [4+2] Cyclization of N-Aryl-α-amino Acids for Synthesizing Polysubstituted Tetrahydroquinolines

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