Dearomatization of indoles via palladium-catalyzed carbonylation using Co2(CO)8 as the carbonyl source leading to carbonyl-containing spiroindolenines DOI
Weiming Hu,

Jiali Huang,

Wenting Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5242 - 5247

Published: Jan. 1, 2023

A Pd-catalyzed carbonylative dearomatization of indoles using Co 2 (CO) 8 as a safe CO source has been reported.

Language: Английский

Enantioselective Construction of Spirooxindole‐γ‐butyrolactones via NHC‐Bound Isobenzofulvene [10π+2π] Cycloaddition DOI

Shuixiu Su,

Ying Chen, Qiyu Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 12, 2025

Comprehensive Summary We report an N ‐heterocyclic carbene (NHC)‐catalyzed [10π+2π] cycloaddition between indene‐2‐carbaldehydes and isatins, delivering spirooxindole‐γ‐butyrolactones with moderate yields (up to 68%) excellent enantioselectivity 93% ee). This transformation proceeds via NHC‐bound isobenzofulvene intermediates represents the first successful application of all‐carbon higherene in NHC‐catalyzed cycloadditions.

Language: Английский

Citations

0
Carbene-Catalyzed Enantioselective Petasis-Like Alkenylation DOI
Zhipeng Li, Jingyang Zhang, Yani Li

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(3), P. 2003 - 2013

Published: Jan. 23, 2024

The N-heterocyclic carbene (NHC)-catalyzed enantioselective Petasis-like alkenylation of o-hydroxycinnamaldehydes or hydroxyl-tethered α,β-unsaturated aldehydes with styryl, dienyl, trienyl boronic acids is disclosed. This method involves the addition π-system-containing to NHC-bounded acyl azoliums and allows access divergent assembly β-alkenyl substituted dihydrocoumarin γ- δ-lactones. DFT calculations suggest that an unprecedented zwitterionic intermediate 1,4- 1,5- migration alkenyl groups play a crucial role in reaction. More in-depth studies orbital noncovalent interaction analysis provide more detailed explanations for pathways stereoselectivity control.

Language: Английский

Citations

2
Palladium-Catalyzed Carbonylative Dearomatization of Indoles to Achieve Carbonyl-Containing Spirocyclic Indolenines Bearing an All-Carbon Quaternary Center DOI
Weiming Hu,

Jiali Huang,

Jingyu Yao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 5951 - 5956

Published: Aug. 3, 2023

A Pd-catalyzed carbonylative dearomatization via an acyl Pd complex has been developed. Diversified carbonyl-containing spirocyclic indolenines with all-carbon quaternary center were constructed in efficient and straightforward way good to excellent yields. The protocol features a simple catalytic system, operational simplicity, broad substrate scope, easy scale-up, versatile transformations. In addition, the asymmetric reaction was initially explored moderate enantioselectivity.

Language: Английский

Citations

6
Synergistic Sc(III)/Au(I)-Catalyzed Dearomative Spiroannulation of 2-(Ethynyl)aryl Cyclopropanes with 2-Aryl Indoles DOI
Jun‐An Xiao,

Hai Peng,

Huan Zhang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(47), P. 8709 - 8713

Published: Nov. 18, 2022

The diastereoselective assembly of spiroindolenines via a synergistic scandium/gold-catalyzed dearomative spiroannulation is herein described. This protocol offers access to wide variety spiroindolenine derivatives in 86% average yield with moderate excellent diastereoselectivities (up 97:3 dr). control experimental studies lend support the bimetallic relay catalysis. Moreover, scale-up reaction and synthetic transformations product further demonstrate its utility.

Language: Английский

Citations

8
Mechanisms, regio- and stereoselectivities involved in NHC catalyzed dearomatizing annulation of ester with ylide: A computational study DOI
Yan Li, Junjie Xiao,

Yanlong Kang

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 560, P. 114146 - 114146

Published: April 16, 2024

Language: Английский

Citations

1
Benzoyl cyanide, a general radical acylating reagent for photoredox-catalyzed benzylic site-selective acylation reactions DOI
Zhaodong Zhu, Jingjing Wu

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(11), P. 3833 - 3843

Published: Sept. 23, 2024

Language: Английский

Citations

0
Enantioselective synthesis of 6-(Indole-2-yl)-3,4-dihydropyran-2-one skeletons by N-Heterocyclic carbene-catalyzed asymmetric [3 + 3] cycloaddition of α-bromocinnamaldehyde DOI Open Access
He Gao, Xiaoyu Chen,

Siqi Xia

et al.

Chemical Synthesis, Journal Year: 2023, Volume and Issue: 3(4)

Published: July 21, 2023

The enantioselective construction of chiral 6-(indole-2-yl)-3,4-dihydropyran-2-one skeleton was demonstrated by the formal [3 + 3] cycloaddition reaction α-bromocinnamaldehyde with β-ketoester indole catalyzed N -heterocyclic carbene (NHC). proceeds smoothly via a vinyl acyl azolium intermediate (electron-poor enone) generated from NHC-aldehyde adducts, providing derivatives in good yields excellent enantioselectivities (up to 98% ee ).

Language: Английский

Citations

1
Dearomatization of indoles via palladium-catalyzed carbonylation using Co2(CO)8 as the carbonyl source leading to carbonyl-containing spiroindolenines DOI
Weiming Hu,

Jiali Huang,

Wenting Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5242 - 5247

Published: Jan. 1, 2023

A Pd-catalyzed carbonylative dearomatization of indoles using Co 2 (CO) 8 as a safe CO source has been reported.

Language: Английский

Citations

1