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

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5242 - 5247

Опубликована: Янв. 1, 2023

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

Язык: Английский

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

Shuixiu Su,

Ying Chen, Qiyu Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 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.

Язык: Английский

Процитировано

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

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(3), С. 2003 - 2013

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2023, Номер 25(32), С. 5951 - 5956

Опубликована: Авг. 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2022, Номер 24(47), С. 8709 - 8713

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

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

и другие.

Molecular Catalysis, Год журнала: 2024, Номер 560, С. 114146 - 114146

Опубликована: Апрель 16, 2024

Язык: Английский

Процитировано

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

Science China Chemistry, Год журнала: 2024, Номер 67(11), С. 3833 - 3843

Опубликована: Сен. 23, 2024

Язык: Английский

Процитировано

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

и другие.

Chemical Synthesis, Год журнала: 2023, Номер 3(4)

Опубликована: Июль 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 ).

Язык: Английский

Процитировано

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5242 - 5247

Опубликована: Янв. 1, 2023

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

Язык: Английский

Процитировано

1