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

Thianthrenation-Promoted Photoinduced Alkene Difunctionalization and Aryl Allylation with Morita-Baylis-Hillman Adducts DOI
Biplab Mondal, Ayan Chatterjee, Nitis Chandra Saha

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An organophotoredox-catalyzed alkoxyallylation of feed-stock olefins, through thianthrenation using a Morita–Baylis–Hillman adduct as an allylating agent, is described.

Language: Английский

Citations

2
Base-Mediated Divergent Synthesis of Spiro-heterocycles Using Pronucleophiles and Ethylene via Thianthrenation DOI

Hongru Wu,

Jie Wang,

Haochuan Jing

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5415 - 5419

Published: June 25, 2024

Spirocyclic compounds are abundant in biologically active products. However, the divergent synthesis of spirocyclic using low-cost and available starting materials remains a challenge. Herein, we report an effective method for producing motifs cyclic β-carbonyl ester or amide ethylene via thianthrenation. This strategy highlights exciting possibility utilizing as C-2 synthon allows regulating core structure compound by simply altering base type.

Language: Английский

Citations

2
Nucleophilic functionalization of thianthrenium salts under basic conditions DOI Creative Commons

Xinting Fan,

Duo Zhang,

xiangchuan xiu

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 257 - 263

Published: Feb. 8, 2024

In recent years, S-(alkyl)thianthrenium salts have become an important means of functionalizing alcohol compounds. However, additional transition metal catalysts and/or visible light are required. Herein, a direct thioetherification/amination reaction thianthrenium is realized under metal-free conditions. This strategy exhibits good functional-group tolerance, operational simplicity, and extensive range compatible substrates.

Language: Английский

Citations

1
Radical Difunctionalization of Unsaturated Hydrocarbons Employing the Same Functional Reagent DOI

Wen‐Chan Tian,

Nan‐Nan Dai,

Yunpeng Lu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3524 - 3541

Published: July 3, 2024

Abstract The radical difunctionalization of unsaturated hydrocarbons serves as an efficient means to rapidly construct molecular skeletons and synthesize‐highly valuable compounds. In this transformational process, diverse positions within are sequentially functionalized by a single precursor reagent, thereby achieving highly selective transformations that promote atom economy. Furthermore, approach minimizes the generation numerous byproducts stemming from cross‐coupling reactions between reactants, owing reduction number participating components. Therefore, review provides in‐depth analysis utilizing functional reagent in recent decades. discussion is based on eight different classes (carbon‐, nitrogen‐, phosphine‐, oxygen‐, sulfur‐, selenium‐, tellurium‐, chlorine‐centered radicals), emphasizing mechanism specific difunctionalization. It also analyzes detail regulation key factors such regional selectivity, unique insights into reaction transformations.

Language: Английский

Citations

1
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

1