Substituent-Dependent, Switchable Synthesis of Nonaromatic and Aromatic Heterocyclic Sulfones Using Visible Light DOI

Mithu Roy,

Itu Mallick,

Manas Mohan Mahapatra

и другие.

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9357 - 9362

Опубликована: Окт. 23, 2024

In this Letter, we described a visible-light-induced switchable synthesis of nonaromatic and aromatic sulfonyl heterocycles. The product selectivity between 2,5-dihydropyrrole pyrrole can be tuned by altering the substituent on N atom 1,6-diyne. We highlight intricacy efficiency approach in constructing molecular frameworks under mild conditions with high functional group tolerance. This study elucidates mechanism underlying selectivity, highlighting its potential as compelling alternative to traditional synthetic techniques.

Язык: Английский

Co(III)-Catalyzed Coupling of Enaminones with Oxadiazolones for Imidazole Synthesis DOI

Shuaixin Fan,

Wei-Ping Wu,

Yachun Su

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Авг. 30, 2024

Appendage speciation-oriented synthesis, as opposed to the conventional wisdom of skeleton is reported herein, emphasizing maximization type-, position-, and configuration-variance appendages. A Co(III) catalytic protocol in accordance with this synthetic modality has been established for coupling enaminones oxadiazolones imidazoles, allowing achievement full position-variance This translates an expanded reaction structural development scope can provide fertile ground productive organic synthesis.

Язык: Английский

Процитировано

5
Synthesis of Tetrasubstituted Pyrroles via DBU-Mediated Cyclization of Unactivated Propargyl Tertiary Amines DOI
Pengyu Zhou, Tiantian Zhang, Q. Richard Lu

и другие.

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

Опубликована: Март 10, 2025

Compared with the well-developed cyclization of functionalized propargylamines, use unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted via a DBU-mediated intramolecular cycloaddition N-alkyl propargylamines. This reaction employs dihydropyrrole intermediates, followed by oxidation produce in presence 2,3-dichloro-5,6-dicyano-p-benzoquinone. In addition, broad substrate scope, high atom economy, selectivity, and simple operation are also advantages this protocol.

Язык: Английский

Процитировано

0
A Concise Formal Synthesis of Bufogargarizin B DOI

Yuxing Xie,

Huiling Yang,

Yuxuan Tang

и другие.

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
B(C6F5)3-Catalyzed Reductive Deoxygenation of Isatins for Indole Synthesis DOI
Steven F. Son,

Hoe Young Choi,

Haye Min Ko

и другие.

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

Опубликована: Апрель 10, 2025

An efficient method for reductive deoxygenation of isatin derivatives using catalyst B(C6F5)3 and methylphenylsilane is described. This reaction proceeds rapidly under mild conditions, the protocol provides a broad substrate scope. Notably, while general synthetic methods utilizing combination hydrosilanes smoothly reduce indoles to generate indolines, present strategy represents first formation without further reduction.

Язык: Английский

Процитировано

0
Radical‐Enabled Dehydrogenative Aromatization: Forging Functionalized Aromatics from Aliphatic Architectures at Ambient Temperature DOI
Xiaoyi Chen, Wei Shu

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Июнь 13, 2024

Abstract Functionalized arenes, such as aniline and phenol derivatives, are important structures in natural products, drug molecules, functional materials. Thus, the development of methods for efficient synthesis functionalized arenes from different precursors under mild conditions have been a long‐term topic organic related areas. To date, great efforts devoted Ar−X bond‐forming processes aromatic precursors. In addition, aliphatic architectures represents an attractive yet challenging alternative to access which construct aromatization during reaction process along with formation C−X bonds. Recently, new strategy non‐aromatic enabled by radicals has received considerable attention direction broader at room temperature.

Язык: Английский

Процитировано

1
Therapeutic potential of isoniazid carbohydrazide derivatives as a promising anti-inflammatory and anti-diabetic drug via synthesis, characterization, biological screening, and computational studies DOI

Krishnakumar Ranganathan,

Meenakshi Srinivasan, Maqusood Ahamed

и другие.

Journal of Molecular Structure, Год журнала: 2024, Номер unknown, С. 141106 - 141106

Опубликована: Дек. 1, 2024

Язык: Английский

Процитировано

1
Boosting Turnover in the Triarylborane-Catalyzed Hydrogenation of N-Substituted Indoles via Olefin-to-Nitrogen Lewis Base Switching in H2-Cleavage Steps DOI Creative Commons
Taiki Hashimoto, Masato Tanigawa,

Kimitaka Kambe

и другие.

Precision Chemistry, Год журнала: 2024, Номер 3(3), С. 128 - 134

Опубликована: Дек. 18, 2024

The shelf-stable heteroleptic borane B(2,6-Cl2C6H3)(3,5-Br2-2,6-F2C6H)2 (B7) efficiently catalyzes the solvent-free hydrogenation of various substituted indoles to indolines with an unprecedented turnover number 8,500, which is more than 400-fold higher that reported for B(C6F5)3 under diluted conditions. Mechanistic studies revealed this proceeds via olefin-to-nitrogen switching Lewis bases involved in H2-cleavage steps: initially, H2 cleavage mediated by a frustrated pair (FLP) comprising indole C3-carbon and boron atoms, then switches FLP system indoline nitrogen atoms after formation indoline. This study demonstrates potential relatively benign main-group elements catalytic synthesis valuable N-containing molecules using H2.

Язык: Английский

Процитировано

1
Hydride Shuttle Catalysis: From Conventional to Inverse Mode DOI Creative Commons
Iakovos Saridakis, Immo Klose, Benjamin T. Jones

и другие.

JACS Au, Год журнала: 2024, Номер 4(9), С. 3358 - 3369

Опубликована: Авг. 19, 2024

Hydride shuttle catalysis has emerged as a powerful synthetic platform, enabling the selective formation of C–C bonds to yield sp3-rich structures. By virtue compelling reactivity sterically encumbered Lewis acids from frustrated pair regime, hydride enables regioselective functionalization alkyl amines at either α- or β-position. In contrast classical acid reactivity, increased steric hindrance prevents interaction with basic amine itself, instead leading reversible abstraction α-carbon. The created positive charge facilitates occurrence transformations before rebound similar capture event happen. this Perspective, we outline broad selection featuring catalysis, well recently developed approach inverse catalysis. Both strategies give rise wide array functionalized and offer elegant approaches otherwise elusive bond formations.

Язык: Английский

Процитировано

0
Substituent-Dependent, Switchable Synthesis of Nonaromatic and Aromatic Heterocyclic Sulfones Using Visible Light DOI

Mithu Roy,

Itu Mallick,

Manas Mohan Mahapatra

и другие.

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9357 - 9362

Опубликована: Окт. 23, 2024

In this Letter, we described a visible-light-induced switchable synthesis of nonaromatic and aromatic sulfonyl heterocycles. The product selectivity between 2,5-dihydropyrrole pyrrole can be tuned by altering the substituent on N atom 1,6-diyne. We highlight intricacy efficiency approach in constructing molecular frameworks under mild conditions with high functional group tolerance. This study elucidates mechanism underlying selectivity, highlighting its potential as compelling alternative to traditional synthetic techniques.

Язык: Английский

Процитировано

0