Selective C–C bond formation from rhodium-catalyzed C–H activation reaction of 2-arylpyridines with 3-aryl-2<i>H</i>-azirines

Baek, Yonghyeon; Kim, Jin-Woo; Jung, Seung Jin; Ryu, Ho Jin; Kim, Su Yeon; Son, Jeong‐Yu; Um, Kyusik; Han, Sang Hoon; Seo, Hyung Jin; Heo, Juyoung; Lee, Kooyeon; Baik, Mu‐Hyun; Lee, Phil Ho

doi:10.1039/c8sc05142a

Cited by 17 publications

(5 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Despite broad substrate scope, electron-deficient arenes were less compatible requiring higher temperature and excess arenes to achieve desirable yields. A Rh-catalyzed coupling of 2-arylpyridines and 3-aryl-2 H -azirines was reported in TFE for the synthesis of acylmethyl-substituted 2-arylpyridine derivatives . During reaction optimization, TFE proved optimal to other solvents, including HFIP.…”

Section: C–h Functionalization Reactionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

View full text Add to dashboard Cite

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

show abstract

Section: C–h Functionalization Reactionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Azirine ring-expansion reactions, leading to 4- and 7-membered heterocycles as well as to ortho -fused systems, are found to a much lesser extent in the literature. Almost all the intermolecular reactions of azirines leading to ortho -fused heterocycles are the annulation reactions of an aromatic 5- or 6-membered ring to the aromatic benzene or pyridine system (Scheme , reactions 1–3). − Only two reactions of 2 H -azirines, resulting in the fusion of a nonaromatic ring, namely the dihydropyrazine ring (reaction 4) and 3 H -azepine ring (reaction 5), with aromatic systems, are known. In all of these processes, azirines undergo a ring opening across the N–C2 or N–C3 bond, usually under metal catalysis, and allow the incorporation of a three-atom C–C–N fragment into the target heterocycle.…”

mentioning

confidence: 99%

2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives

et al. 2019

View full text Add to dashboard Cite

A method of furo-annulation of 4-hydroxy-2oxoquinoline-3-carboxylates with 3-arylazirines under Cu(II) catalysis was developed to synthesize a variety of 2,3dihydrofuro[3,2-c]quinolones bearing a carbamate group at the C2 position. The reaction involves an azirine ring opening across the N−C2 bond and formation of a dihydrofuran ring with the inclusion of two azirine carbon atoms, accompanied by a shift of the ester group to the nitrogen. The discovered reaction is the first example of the use of 2H-azirines for furo-annulation.

show abstract

“…Owing to the successful experience in CÀ H activation with a directing group strategy, Lee et al [145] discovered the Rhcatalyzed ring-opening of 3-aryl-2H-azirines, followed by CÀ C coupling to give acylmethyl-substituted 2-arylpyridine derivatives. This methdology was innovatively guided by DFTcalculations.…”

Section: Ring-opening Of 2h-azirines To Acyclic Compoundsmentioning

confidence: 99%

2H‐Azirines: Recent Progress in Synthesis and Applications

Xu,

Zeng,

Luo

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

2H‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances in the synthesis and functionalization of 2H‐arizines have been reported. Neber rearrangement, isomerization of isoxazole, oxidation of enamine, C–H bond activation, decomposition of vinyl azide, functionalization of alkyne, and multi‐step synthesis have been developed for the efficient assembly of 2H‐azirines. As versatile and highly strained three‐membered unsaturated heterocycles, 2H‐azirines can be used as distinctive building blocks towards significant functional groups, and have attracted extensive attention for the fabrication of numerous heterocycles. Recent studies have focused on [3+n] ring‐expansion reactions, nucleophilic addition of C=N double bond or continuous nucleophilic addition followed by cyclization, ring‐opening of 2H‐azirines to acyclic compounds, and substitution of sp3‐C‐H of 2H‐azirines. One of the most critical challenges is seeking for a selective opening of the specific three bonds of the strained azirine circle, some of what can be achieved on the basis of metal catalyst, photocatalysis, or combination of metal catalyst and photocatalysis. In this review, recent advances involving the synthesis and reactivity of 2H‐arizines accompanied with challenges and breakthroughs are summarized. The review mainly covers the period from 2019 to 2023.

show abstract

Selective C–C bond formation from rhodium-catalyzed C–H activation reaction of 2-arylpyridines with 3-aryl-2H-azirines

Abstract: A novel method for the synthesis of acylmethyl-substituted 2-arylpyridine derivatives using 3-aryl-2H-azirines was developed.

Cited by 17 publications

References 58 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives

2H‐Azirines: Recent Progress in Synthesis and Applications

Contact Info

Product

Resources

About