Asymmetric Synthesis of 2-Arylethylamines: A Metal-Free Review of the New Millennium DOI Creative Commons
Alejandro Manchado, Ángel García-González, Carlos T. Nieto

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5729 - 5729

Published: Dec. 4, 2024

2-Arylethylamines are presented in several natural bioactive compounds, as well nitrogen-containing drugs. Their ability to surpass the blood-brain barrier makes this family of compounds especial interest medicinal chemistry. Asymmetric methodologies towards synthesis 2-arylethylamine motives great due challenges they may present. Thus, a concise metal-free review presenting recent advances asymmetric 2-arylethylamines is presented, covering last-millennium studies, considering different aforementioned motif, including chiral induction, organocatalysis, organophotocatalysis and enzymatic catalysis.

Language: Английский

Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes DOI Creative Commons
Stefano Bonciolini, Antonio Pulcinella, Matteo Leone

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Feb. 19, 2024

In contemporary drug discovery, enhancing the sp

Language: Английский

Citations

20
Merging SOMO activation with transition metal catalysis: Deoxygenative functionalization of amides to β-aryl amines DOI Creative Commons

Tian Hongjun,

Feng Jiang,

Xiaoming Wang

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(3)

Published: Jan. 17, 2025

Singly occupied molecular orbital (SOMO) activation of in situ generated enamines has achieved great success (asymmetric) α-functionalization carbonyl compounds. However, examples on the use this mode transformations other functional groups are rare, and combination SOMO with transition metal catalysis is still less explored. In area deoxygenative functionalization amides, intermediates such as iminium ions were often to result formation α-functionalized amines. contrast, direct deoxygenation amides β-functionalized amines highly appealing yet remains scarcely investigated. Here, a arylation aryl halides was developed via multicatalysis iridium/photoredox/nickel/iridium, affording β-aryl high efficiency. The key reaction enamine synergy Ni-catalyzed arylation, which conjunction two compatible Ir-catalyzed reduction processes.

Language: Английский

Citations

1
A General Amino–(Hetero)arylation of Simple Olefins with (Hetero)aryl Sulfonamides Enabled by an N-Triazinyl Group DOI

Jaxon L. Barney,

Andrew J. Wolfram,

Rose Litvak

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 2139 - 2149

Published: Jan. 22, 2025

(Hetero)arylethylamines are privileged substructures in pharmaceuticals, agrochemicals, and other bioactive compounds. In principle, the amino–(hetero)arylation of olefins represents an ideal strategy for rapid preparation these pharmacophores, which could accelerate discovery valuable new products. Established methods, however, do not accommodate several important classes (hetero)aromatic structures, precludes access to appreciable range molecular architectures. To address limitations, we have developed a radical-mediated reaction that adds amino (hetero)aryl groups from simple stable sulfonamide across alkene. The identification readily available triazine as original N-protecting group was critical development this transformation. features good regio- stereoselectivity succeeds with medicinally unproductive alternate protocols. Lastly, highlighted advances by synthesizing TMP269, class IIa histone deacetylase inhibitor would otherwise be challenging prepare olefin amino–arylation.

Language: Английский

Citations

0
Nickel-Catalyzed Asymmetric Homobenzylic Hydroamidation of Aryl Alkenes to Access Chiral β-Arylamides DOI
Xiang Lyu,

Eunmi Jeon,

Changhyeon Seo

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

Herein, we introduce a Ni-catalyzed asymmetric homobenzylic hydroamidation reaction that efficiently addresses the dual challenges of achieving regio- and enantioselectivity in synthesis β-(hetero)arylethylamides. By employing transposed NiH catalysis approach, this method facilitates formation key chiral nickel-amido intermediates, enabling insertion into alkenes to produce desired β-arylamide products with excellent enantioselectivity. The exhibits high functional group tolerance utilizes readily available starting materials vinylarenes react dioxazolone as robust amidating source. Notably, approach was successfully applied pharmaceutical compounds natural products, such Clobenzorex, Direx, Selegiline, Sacubitril, Cipargamin.

Language: Английский

Citations

0
Discovery of N-substituted-2-((arylethyl)amino)-2-(2-methoxyphenyl) acetamides: A novel family of antiplatelet agents DOI
Lyanne Rodríguez,

Carlos Rodríguez,

Jhonny Azuaje

et al.

Biomedicine & Pharmacotherapy, Journal Year: 2025, Volume and Issue: 186, P. 117971 - 117971

Published: March 17, 2025

Language: Английский

Citations

0
Mannich Reaction of Secondary Benzylzinc Reagents: Synthesis of α,β‐Disubstituted β‐Arylethylamines DOI Creative Commons

Baptiste Leroux,

Federico Banchini, Olivier Jackowski

et al.

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

Abstract The organometallic multicomponent Manich reaction of secondary benzylzinc compounds is described. These reagents were efficiently prepared by direct metalation (1‐bromoethyl)benzenes in tetrahydrofuran with zinc dust. Their subsequent Mannich coupling amines and aldehydes allowed the straightforward preparation a large variety α,β‐disubstituted β‐arylethylamines yields ranging from 13% to 79%. This was found require use heated mixture acetonitrile, being essential reach good acetonitrile ensuring reproducibility.

Language: Английский

Citations

0
Visible‐Light‐Induced Metal‐Free Three‐Component Amidoheteroarylation of Alkenes to Synthesize β‐(Hetero)arylethylamines DOI

Qiange Feng,

He Wang, Yang Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(19)

Published: March 21, 2024

Abstract Herein, visible‐light‐induced metal‐free three‐component amidoheteroarylation of alkenes with quinoxalin‐2(1 H )‐ones and N‐sulfonylaminopyridinium salts is developed. This protocol involves a radical relay process in which the N‐centered radicals undergo chemoselective addition to form an alkyl that selectively combines heteroarenes, leading formation C−C C−N bonds one step under mild reaction conditions. The involved high efficiency selectivity, wide substrate scope, excellent functional‐group compatibility demonstrate practicability developed protocol.

Language: Английский

Citations

3
Transition metal-free difunctionalization of unactivated alkenes: Arylation/azidation, arylation/chlorination, and arylation/cyanation DOI
Li Li, Viresh H. Rawal

Chem, Journal Year: 2024, Volume and Issue: 10(10), P. 3243 - 3253

Published: Sept. 2, 2024

Language: Английский

Citations

3
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

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 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.

Language: Английский

Citations

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

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 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.

Language: Английский

Citations

0