Deaminative Arylation of Amino Acid-derived Pyridinium Salts

Hoerrner, Megan E.; Baker, Kristen M.; Basch, Corey H.; Bampo, Earl M.; Watson, Mary P.

doi:10.1021/acs.orglett.9b02643

Cited by 69 publications

(28 citation statements)

References 55 publications

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“…Subsequently,slight modifications of the method also enabled the cross-coupling of benzylic amines with aryl and vinylboronic acids, [31] as well as amino acid derived pyridinium salts with aryl boroxines. [32] Additionally, N-alkyl pyridinium salts 1 were also shown to undergo efficient nickel-catalyzed Negishi cross-coupling reactions with alkylzinc reagents for the generation of C(sp 3 ) À C(sp 3 )bonds. [33] In contrast to Suzuki coupling,the use of atridentate ligand for nickel proved critical for alkyl-alkyl coupling.…”

Section: N-carbon-substituted Pyridinium Reagentsmentioning

confidence: 99%

Pyridinium Salts as Redox‐Active Functional Group Transfer Reagents

et al. 2020

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In this Review, we highlight recent advances in the understanding and design of N‐functionalized pyridinium scaffolds as redox‐active, single‐electron, functional group transfer reagents. We provide a selection of representative methods that demonstrate reactivity and fundamental advances in this emerging field. The reactivity of these reagents can be divided into two divergent pathways: homolytic fragmentation to liberate the N‐bound substituent as the corresponding radical or an alternative heterolytic fragmentation that liberates an N‐centered pyridinium radical. A short description of the elementary steps involved in fragmentation induced by single‐electron transfer is also critically discussed to guide readers towards fundamental processes thought to occur under these conditions.

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Section: N-carbon-substituted Pyridinium Reagentsmentioning

confidence: 99%

Pyridinium Salts as Redox‐Active Functional Group Transfer Reagents

et al. 2020

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“…Watson and co-workers also explored the Ni-catalyzed arylation of amino acid derived pyridinium salts (Scheme 14). 56 Different hydrochlorides of amino esters were converted into the corresponding pyridinium salts in high yields and subsequent arylation gave propanoic acid derivatives which are known for their nonsteroidal anti-inflammatory activity.…”

Section: Scheme 13 Reductive Cross-couplings Using Alkyl Katritzky Saltsmentioning

confidence: 99%

Pyrylium Salts: Selective Reagents for the Activation of Primary Amino Groups in Organic Synthesis

2019

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Primary amino groups represent an ubiquitous category of functionalities in synthetic building blocks, drugs, and natural products. Therefore, such functionalities offer themselves as perfect handles for late-stage functionalization, and the development of robust and efficient strategies to transform these groups is highly desirable. Despite the extremely challenging activation of the C–N bond, the past few years have witnessed the rapid development of deaminative transformations using pyrylium salts as activating reagents. In most cases, the pyridinium salts formed were activated by single electron transfer, giving alkyl radicals which were used in a series of transformations via nickel and photoredox catalysis. This short review aims to give an overview to related properties of pyrylium salts, their historical significance, and summarize the recent progress in the field of deaminative transformations using these reagents.1 Introduction2 Pyrylium and Pyridinium Salts2.1 Historical Context2.2 Structure and Reactivity2.3 Pyrylium Synthesis2.4 Historical Context of the Reactivity of Pyridinium Salts3 Recent Progress on Deaminative Transformations of Primary Amino Groups by Pyrylium Salts3.1 Metal-Catalyzed Cross-Couplings3.2 Photoredox Catalysis and Photoinduced Reactions for C–C Bond Constructions3.3 Borylations3.4 SNAr Functionalization of Aminoheterocycles4 Conclusion

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“…In addition, the electronic nature of the substituents of (hetero)aryl boronic acids had no great influence on the reaction. Later, the same groups demonstrated that the deaminative arylation could be extended to benzylic amines [27] (Scheme 14) and amino acids [28] (Scheme 15) with arylboronic reagents under modified conditions. Various diarylmethanes and α-aryl esters could be prepared in moderate to good yields, respectively.…”

Section: (Hetero)arylation Of Katritzky Saltsmentioning

confidence: 99%

Recent Developments in Deaminative Functionalization of Alkyl Amines

Xiao

Guo

et al. 2021

Eur J Org Chem

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The amino group is one of the most prevalent functional groups present in a wide range of organic molecules, which has been widely applied in various organic synthesis and pharmaceuticals. Alkyl amines could be converted in a single step into Katritzky salts which could serve as alkyl radical precursors to construct CÀ C bonds and CÀ X bonds via C(sp 3)À N cleavage. This deaminative functionalization could be carried out under transition-metal catalysis, photocatalysis, carbene catalysis or promoted by base. In this paper, recent developments in the deaminative functionalization of alkyl amines were covered. This review was categorized into four parts according to the nature of the bond formation. Some representative examples and corresponding reaction mechanisms were also summarized.

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Deaminative Arylation of Amino Acid-derived Pyridinium Salts

Cited by 69 publications

References 55 publications

Pyridinium Salts as Redox‐Active Functional Group Transfer Reagents

Pyridinium Salts as Redox‐Active Functional Group Transfer Reagents

Pyrylium Salts: Selective Reagents for the Activation of Primary Amino Groups in Organic Synthesis

Recent Developments in Deaminative Functionalization of Alkyl Amines

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