Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines DOI Creative Commons
Valentyn Pozhydaiev,

Antonio Paparesta,

Joseph Moran

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(45)

Опубликована: Июль 17, 2024

Abstract 1,2‐Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N‐functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2‐diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N ‐heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2‐aminothiolation styrenes.

Язык: Английский

Rearrangement and Cyclization of Enamine Thianthrenium Salts: Effective Access to Substituted Indoles DOI
Zhixin Ren,

C. Deng,

Zijing Bai

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 2, 2025

A facile base-mediated cyclization and rearrangement of enamine thianthrenium salts for the construction indole compounds is disclosed. In this reaction, sequential cleavage two C-S bonds subsequent formation C-N C-C furnish a series substituted indoles in moderate to good yields. Furthermore, an efficient late-stage functionalization established. The method features wide substrate scope, functional group tolerance, low-cost starting materials.

Язык: Английский

Процитировано

0

A Neutral PCNHCP Co(I)–Me Pincer Complex as a Catalyst for N-Allylic Isomerization with a Broad Substrate Scope DOI Creative Commons
Sakthi Raje,

Tofayel Sheikh Mohammad,

Graham de Ruiter

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4319 - 4325

Опубликована: Март 23, 2024

Earth-abundant-metal catalyzed double bond transposition offers a sustainable and atom-economical route toward the synthesis of internal alkenes. With an emphasis specifically on olefins ethers, isomerization allylic amines has been particularly under represented in literature. Herein, we report efficient methodology for selective N-allylic organic compounds, including amines, amides, imines. The reaction is by neutral PCNHCP cobalt(I) pincer complex proceeds via π-allyl mechanism. occurs readily at 80–90 °C, it compatible with wide variety functional groups. situ formed enamines could additionally be used one-pot inverse-electron-demand Diels–Alder to furnish series diversely substituted heterobiaryls, which further discussed this report.

Язык: Английский

Процитировано

2

Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines DOI Creative Commons
Valentyn Pozhydaiev,

Antonio Paparesta,

Joseph Moran

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)

Опубликована: Июль 17, 2024

1,2-Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N-functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2-diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N-heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2-aminothiolation styrenes.

Язык: Английский

Процитировано

2

Chiral trifluoromethylated enamides: Synthesis and applications DOI Creative Commons
Alexandru Postole, Pablo Martínez‐Pardo, Víctor García‐Vázquez

и другие.

Chem Catalysis, Год журнала: 2023, Номер 3(12), С. 100813 - 100813

Опубликована: Ноя. 14, 2023

Enamides are versatile building blocks in organic synthesis that give access to complex nitrogen-containing compounds. However, despite the interest these compounds, synthetic strategies enamides with carbon-centered chirality atre scarce. In this work, we report an efficient method for of a new class chiral trifluoromethylated stereogenic center from easily accessible allylic amines by effective chirality-transfer process. The gives excellent yields and diastereo- enantioselectivities. scope reaction is broad, various substituents functional groups tolerated. Furthermore, transformations were carried out trifluoromethylated, structures. For example, photocatalytic E/Z isomerization also presented.

Язык: Английский

Процитировано

5

Development of Efficient Synthetic Reactions Using Enamines and Enamides Carrying Oxygen Atom Substituent on Nitrogen Atom DOI Open Access
Okiko Miyata

Chemical and Pharmaceutical Bulletin, Год журнала: 2024, Номер 72(5), С. 432 - 453

Опубликована: Апрель 30, 2024

We have developed efficient synthetic reactions using enamines and enamides carrying oxygen atom substituent on nitrogen, such as N-alkoxyenamines, N,α-dialkoxyenamines, N-alkoxyanamides, N-(benzoyloxy)enamides. The umpolung reaction by polarity inversion at the β-position of N-alkoxyenamines afforded α-alkyl-, α-aryl-, α-alkenyl-, α-heteroarylketones aluminum reagent nucleophiles. Furthermore, one-pot α-phenylation ketones has been also developed. applied this method to N,α-dialkoxyenamine, generated from N-alkoxyamide afford α-arylamides. vicinal functionalization achieved with formation two new carbon–carbon bonds an organo-aluminum subsequent allyl magnesium bromide or tributyltin cyanide. A sequential retro-ene arylation for conversion N-alkoxyenamides corresponding tert-alkylamines. [3,3]-sigmatropic rearrangement N-(benzoyloxy)enamides followed cyclic β-aryl-β-amino alcohols bearing a tetrasubstituted carbon center. resulting products were converted into sterically congested β-amino alcohols, well dissociative anesthetic agent Tiletamine.

Язык: Английский

Процитировано

1

Catalyst-Free Radical Carbosulfonylation of Enamides with Indoles, Aryldiazonium Tetrafluoroborates, and DABCO·(SO2)2 DOI
Changmei Zhang, Hao Cheng, Yuanyuan An

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Сен. 23, 2024

Herein, we have developed a catalyst-free four-component carbosulfonylation of enamides involving indoles, DABCO·(SO

Язык: Английский

Процитировано

1

Visible-Light-Induced Synthesis of Branched Ethers via Multicomponent Reactions DOI
Nándor Győrfi, Gábor Tasnádi, Márió Gyuris

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 10014 - 10019

Опубликована: Июль 7, 2023

The Spin-Center Shift (SCS) elimination is a specific way for the generation of radicals with relevance in synthetic and biochemical pathways. combination SCS-mediated radical chemistry atom-transfer addition (ATRA) offers new directions diversity-oriented chemical synthesis. Herein, we report photoredox three-component reaction α-acyloxy-N-heterocycles as precursors, styrene derivatives trapping agents, alcohols nucleophilic quenchers. novel radical-polar crossover provides access to diverse set branched ethers possessing high structural complexity. utility transformation was also demonstrated by synthesis complex drug derivative it easily scalable multigram level. scope limitations were explored plausible mechanism proposed.

Язык: Английский

Процитировано

2

Visible-Light-Induced Difunctionalization of the C-C Bond of Alkylidenecyclopropanes with Acyl Chlorides DOI Open Access
Chuan Ding, Peng‐Fei Huang, Biquan Xiong

и другие.

Catalysts, Год журнала: 2023, Номер 13(6), С. 919 - 919

Опубликована: Май 23, 2023

A new and powerful visible-light-induced difunctionalization of the C-C σ-bond alkylidenecyclopropanes via a ring-opening process was developed. Importantly, acyl chlorides are used as both Cl sources. This strategy provides an effective route for bond with radical Cl− to construct C-Cl in one pot. In addition, it has wide range substrates can tolerate various functional groups.

Язык: Английский

Процитировано

1

Structures and Reactivities of N-Alkenyl-Substituted Anilides: The “Magic” Methyl Effect on Alkene DOI
Ryu Yamasaki,

Mariko Ono,

Kento Morita

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(20), С. 14487 - 14493

Опубликована: Сен. 28, 2023

Methyl substitution at the double bond of N-alkenyl anilides influences both preferred conformation and susceptibility to acidic hydrolysis. The R1-substituted amide favors trans conformation, whereas amides substituted R2 or R3 favor cis conformation. Substitution R1 positions increases ratio conformer. DFT study indicated that these conformational preferences can be explained in terms substituent-induced torsion twisting moiety relative plane. enhances hydrolysis, stability. effect on was showcased by contrasting anilide (trans) hydrogenated N-isopropyl (cis).

Язык: Английский

Процитировано

1

I2 or I2/PIFA one‒pot induced system for rapid synthesis of chalcogenated enamides, uracils or 2-pyridones under mild conditions DOI

Hamdi Sanaa,

Ismaël Dondasse,

Pascal Retailleau

и другие.

New Journal of Chemistry, Год журнала: 2024, Номер 48(28), С. 12793 - 12799

Опубликована: Янв. 1, 2024

An I 2 -mediated β-C(sp )–H chalcogenylation of enamides under mild and rapid conditions has been developed. Sequential addition PIFA led to valuable 5-thio- 5-seleno-2-pyridones with a free C3 position.

Язык: Английский

Процитировано

0