N‐Heterocyclic Carbene Catalyzed Reactions Involving Acetylenic Breslow and/or Acylazolium as Key Intermediates DOI Open Access

Yujie He,

Jintao Chen, Yu Jiang

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

N-heterocyclic carbene (NHC) organocatalysis has been developed as a powerful tool in modern synthetic chemistry. NHC catalytic activation of ynals and alkynoic acid derivatives provided versatile reactions that involve acetylenic Breslow and/or acylazolium key intermediates, diverse transformations have established for access to molecules with unique skeletons efficient fashions. Herein we summarize the recent achievements NHC-catalyzed involving intermediates. Different belonging three modes, including (1) conjugate additions derived α,β-unsaturated (2) β-umpolung via (3) are emphasized examples plausible mechanisms cited guide better understanding.

Language: Английский

Enantioselective Cascade Annulation of 1,2,3-Triazoles and Enals Enabled by Sequential Rhodium and Oxidative NHC Catalysis Involving Cleavage, Migration, and Cyclization DOI

Xiaoyi Yu,

Hao An, Wenbin Wu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

The in situ-generated pyrrolin-3-ones serve as novel and versatile synthons, being employed intermediates for the efficient production of pyrrole-fused lactones with high yield excellent enantioselectivity. Herein, we introduce emerging rhodium oxidative N-heterocyclic carbene relay catalysis that enables a highly enantioselective cascade annulation between easily available 1,2,3-triazoles enals. In this proof-of-concept study, engage α,β-unsaturated acylazolium generated from enals via catalysis.

Language: Английский

Citations

1
Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis DOI Creative Commons
Xia Wang, Shaojie Wang,

Xiaolan Xin

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(33), P. 13240 - 13249

Published: Jan. 1, 2024

The enantioselective and diastereoselective synthesis of atropisomeric hydrazides with defined vicinal central axial chirality via ternary catalysis in a one-pot process is reported.

Language: Английский

Citations

4
Asymmetric construction of axial and planar chirality with N-heterocyclic carbene (NHC) organocatalysis DOI
Meng Zhang,

Xiaoqun Yang,

Xiaolin Peng

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Language: Английский

Citations

4
Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and Naphtho[2,3-b]furan-4,9-diones DOI
Xiang Liu, Hexiang Wang, Dongxin Lin

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

A three-component multi-auto-tandem reaction for the construction of site-specific tricyclic furo[3,2-c]coumarins via formation C-C, C-O, and C-S bonds in one step from 4-hydroxycoumarins/4-hydroxy-2-pyrones, ynals, sodium sulfinates is reported. This cascade efficiently produces a variety rare C-2-functionalized moderate to good yields under straightforward conditions. Furthermore, this protocol can be extended coupling involving 2-hydroxy-1,4-naphthoquinone, sulfinates, yielding naphtho[2,3-b]furan-4,9-dione derivatives. Notably, carbonyl group α-position ynals act as C-2 synthons specific reaction, enabling two aforementioned types multicomponent transformations.

Language: Английский

Citations

0
One-Flask, Telescoped Synthesis of Pyrano[3,2-b]indol-2-ones from O-Nitroynones and β-Ketoesters: Further Advancement to Functionalized Carbazoles DOI

K. A. Sudarshana,

Alagesan Balasubramani, Srihari Pabbaraja

et al.

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

Published: March 19, 2025

A new general strategy for accessing pyrano[3,2-b]indol-2-ones, a promising fused hybrid heterocyclic system, has been devised from o-nitroynones and β-ketoesters through one-flask cascade process involving tandem Michael addition, intramolecular cyclization, Cadogan-Sundberg reductive cyclization. The utility of this approach further amplified by leveraging the cycloaddition proclivity α-pyrone moiety in pyrano[3,2-b]indol-2-ones toward concise entry to carbazoles. Illustrative synthesis carbazole natural products hyellazole chlorohyellazole is also disclosed.

Language: Английский

Citations

0
Five-Component [2 + 2 + 1 + 1] Tandem Benzannulation Leading to Multifunctionalized Aromatic Amines DOI
Hexiang Wang,

Shuting Li,

Xiaoying Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9648 - 9653

Published: Nov. 1, 2024

An unprecedented five-component [2 + 2 1 1] benzannulation strategy for regioselective assembly of densely functionalized aromatic amines from two ynals, malononitriles, and sodium sulfinates is established. The protocol enables the efficient installation five substituents on a benzene ring via formation multiple chemical bonds in single operation, providing various multifunctionalized primary moderate to good yields. Additionally, three-component [3 cycloaddition NH4SCN was also achieved produce 2-amnopyridine derivatives with serving as an ammonia surrogate.

Language: Английский

Citations

3
Diastereo- and Enantioselective Chemodivergent Three-Component Cascade Reactions via Gold and Carbene Sequential Catalysis DOI
Shulei Zhang, Shaojie Wang,

Xiaolan Xin

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9275 - 9282

Published: June 4, 2024

This study investigates the feasibility and inherent benefits of combining transition-metal- organoasymmetric-catalyzed reactions in one pot. The reported transformation features Au-catalyzed tandem hydration–oxacyclization NHC-catalyzed enantioselective annulation, effectively converting simple skipped diynones, water, enals into highly diastereo- enantioenriched fused heterocycles. Furthermore, chemoselectivity controlled by base is particularly noteworthy, enabling facile access to ε-lactones or spiro heterocycles from same set starting materials.

Language: Английский

Citations

2
Catalytic Synthesis of 1H-Benzoxazolo[3,2-a]pyridin-1-ones via Formal [3 + 3] Annulations of NHC-Generated Alkynyl Acylazoliums with Benzoxazolyl Acetates and Their Photophysical Studies DOI

Sibasis Sarkar,

Suravi Das,

Shikha Gandhi

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15559 - 15567

Published: Oct. 21, 2024

We disclose the synthesis of a tricyclic fused N-heterocycle via NHC-catalyzed annulation either ynal or an alkynyl ester with readily accessible benzoxazolyl acetate. While ynals requires oxidant, reaction esters proceeds direct generation acylazolium intermediates NHC. With dearth catalytic processes to access these 1H-benzoxazolo[3,2-a]pyridin-1-ones from simple starting materials, this method is especially important. The photophysical properties products have also been evaluated.

Language: Английский

Citations

1
N‐Heterocyclic Carbene Catalyzed Reactions Involving Acetylenic Breslow and/or Acylazolium as Key Intermediates DOI Open Access

Yujie He,

Jintao Chen, Yu Jiang

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

N-heterocyclic carbene (NHC) organocatalysis has been developed as a powerful tool in modern synthetic chemistry. NHC catalytic activation of ynals and alkynoic acid derivatives provided versatile reactions that involve acetylenic Breslow and/or acylazolium key intermediates, diverse transformations have established for access to molecules with unique skeletons efficient fashions. Herein we summarize the recent achievements NHC-catalyzed involving intermediates. Different belonging three modes, including (1) conjugate additions derived α,β-unsaturated (2) β-umpolung via (3) are emphasized examples plausible mechanisms cited guide better understanding.

Language: Английский

Citations

0