N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts

Kim, Inwon; Im, Honggu; Lee, Hyeonyeong; Hong, Sungwoo

doi:10.1039/d0sc00225a

Cited by 137 publications

(56 citation statements)

References 40 publications

(5 reference statements)

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“…In 2020, Hong and co‐workers described a NHC‐Catalyzed radical reaction between Katritzky salts and aldehydes for realizing acylation of α‐amino acids and their derivatives (Scheme 31). [44] In this reaction, the seven‐membered ring fused thiazolium salt was used as the catalyst and Cs 2 CO 3 as the base. Generally, amino acids including glutamic, alanine, homoalanine, valine, norvaline, methionine, phenylalanine, homophenylalanine were well tolerated, affording the deaminative acylation products in moderate to good yields.…”

Section: C(sp3)−c(sp2) Bond Formationmentioning

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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Section: C(sp3)−c(sp2) Bond Formationmentioning

confidence: 99%

Recent Developments in Deaminative Functionalization of Alkyl Amines

Xiao

Guo

et al. 2021

Eur J Org Chem

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“…Jumpei Taguchi and his coworkers have synthetized potassium acyl trifluoroborates from aldehydes through copper (I)-catalyzed borylation/oxidation (Taguchi et al, 2019 (Yabushita et al, 2019;Kakeno et al, 2020). Sungwoo Hong group have employed an N-heterocyclic carbene (NHC) catalyst, which have developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts (Kim et al, 2020).…”

Section: Chiral Aldehyde Catalysis With Transition Metalsmentioning

confidence: 99%

Catalytic Asymmetric Amino Acid and Its Derivatives by Chiral Aldehyde Catalysis

Lin

Shi

et al. 2021

Front. Chem.

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Amine acid transformation is an important chemical process in biological systems. As a well-developed and acknowledged tool, chiral aldehyde catalysis provides good catalytic activation and stereoselective control abilities in the asymmetric reaction of N-unprotected amino acid esters and amino acid esters analogs, in which the key to success is the design of the catalysts derived from chiral BINOL aldehyde, which is based on the face control of enolate intermediates. In this review, one of the co-catalytic systems that combined with a transition metal to form a multiplex catalytic system and the well-established multiplex stereocenters of chiral aldehyde catalysis have been reviewed. Finally, a novel organocatalysis is prospected.

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“…24 In 2020, the Hong group enabled the use of redox active Katritzky pyridinium salts instead of redox active esters in the alkylation of aldehyde and the three-component alkylacylation of alkene (Scheme 14). 25 Katritzky salts can be directly reduced by the enolate form of Breslow intermediate to generate a ketyl radical and an alkyl radical and then radical-radical coupling with two radical species proceeds to yield a ketone.…”

Section: Carbon-carbon Bond Formation Through Set/radical-radical Couplingmentioning

confidence: 99%

Recent advances in N-heterocyclic carbene-based radical catalysis

2020

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N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts

Abstract: By employing an N-heterocyclic carbene (NHC) catalyst, we developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts.

Cited by 137 publications

References 40 publications

Recent Developments in Deaminative Functionalization of Alkyl Amines

Recent Developments in Deaminative Functionalization of Alkyl Amines

Catalytic Asymmetric Amino Acid and Its Derivatives by Chiral Aldehyde Catalysis

Recent advances in N-heterocyclic carbene-based radical catalysis

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