Pd-Catalyzed Dearomative Functionalizations of Benzyl and Aryl Electrophiles DOI
Hiroki Kato, Kei Muto, Junichiro Yamaguchi

и другие.

Journal of Synthetic Organic Chemistry Japan, Год журнала: 2024, Номер 82(10), С. 965 - 978

Опубликована: Окт. 1, 2024

Dearomative functionalization is a powerful method to construct structurally complex alicyclic frameworks from simple and abundant aromatic molecules. Although myriad of dearomative functionalizations have been reported so far, the reaction electron-neutral arenes such as benzenes naphthalenes are still challenging issue due their high stability, often requiring an excess amount starting materials. Recently, we developed catalytic by focusing on unique reactivity π-benzyl palladium catalysis. In this manuscript, describe our endeavor develop C-C bond formations benzyl alcohol derivatives, ammoniums, bromoarenes. The dearomatized compound was transformed into various skeletons diverse derivatizations. Furthermore, successfully achieved C-N formation with bromo(hetero)arenes, resulting in synthesis azaspirocycles. Utilizing present methodology, total Cephalotaxus alkaloids polycyclic skeleton, has also accomplished.

Язык: Английский

Palladium-Catalyzed Domino Heck/Decarboxylative Cyanomethylation of Indoles and Alkenes with Cyanoacetate Salts DOI

Ping‐Xin Zhou,

Yang Liu, Mengjuan Li

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

A palladium-catalyzed reaction of indoles with cyanoacetate salts enables the synthesis 2,6-disubstituted indolines via tandem dearomatization/decarboxylative cyanomethylation. Remarkably, this is first example indole difunctionalization at C2 and C6 positions. Moreover, methodology extends to cyclization/decarboxylative cyanomethylation aryl halide-tethered alkenes.

Язык: Английский

Процитировано

0
6.1 Palladium-Catalyzed Dearomative Functionalization of Arenes DOI
Kei Muto, Junichiro Yamaguchi

Опубликована: Янв. 1, 2025

Abstract Palladium catalysis plays a pivotal role in organic synthesis, encompassing applications cross-couplings and hydrogenations, among other transformations. Recent progress palladium chemistry has helped enable catalytic dearomative functionalizations. In particular, involving benzyl–palladium species been applied to achieve functionalization of wide range aromatic systems, including challenging substrates such as electronically unbiased benzenes, without the need use an excess amount arene starting materials. This review primarily focuses on via species, incorporating these methodologies synthesis natural products.

Язык: Английский

Процитировано

0
Fused Seven-Membered Carbocycle Construction through Electrochemical Relay Cyclization DOI
Wenjing Ma, Yanwei Wang,

Chunhang Zhao

и другие.

Organic Letters, Год журнала: 2024, Номер 26(35), С. 7393 - 7397

Опубликована: Авг. 27, 2024

Seven-membered carbocycles, which are frequently associated with relevant biological activities, can be found in nature and drugs ever-increasing numbers. Radical cascade addition of 1,

Язык: Английский

Процитировано

0
Pd-Catalyzed Dearomative Functionalizations of Benzyl and Aryl Electrophiles DOI
Hiroki Kato, Kei Muto, Junichiro Yamaguchi

и другие.

Journal of Synthetic Organic Chemistry Japan, Год журнала: 2024, Номер 82(10), С. 965 - 978

Опубликована: Окт. 1, 2024

Dearomative functionalization is a powerful method to construct structurally complex alicyclic frameworks from simple and abundant aromatic molecules. Although myriad of dearomative functionalizations have been reported so far, the reaction electron-neutral arenes such as benzenes naphthalenes are still challenging issue due their high stability, often requiring an excess amount starting materials. Recently, we developed catalytic by focusing on unique reactivity π-benzyl palladium catalysis. In this manuscript, describe our endeavor develop C-C bond formations benzyl alcohol derivatives, ammoniums, bromoarenes. The dearomatized compound was transformed into various skeletons diverse derivatizations. Furthermore, successfully achieved C-N formation with bromo(hetero)arenes, resulting in synthesis azaspirocycles. Utilizing present methodology, total Cephalotaxus alkaloids polycyclic skeleton, has also accomplished.

Язык: Английский

Процитировано

0