Synthesis of naphthalene-substituted aromatic esters via Rh(iii)-catalyzed C–H bond naphthylation and cascade directing group transformation DOI
Yue Cui, Siyu Li, Hesheng Wang

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(95), P. 13230 - 13233

Published: Jan. 1, 2022

A regioselective Rh(III)-catalyzed C-H bond naphthylation and cascade directing group (DG) transformation has been realized with aryl imidates oxa bicyclic alkenes. Diverse naphthalene-substituted aromatic esters were synthesized fruitfully. The DG into ester endows the strategy chances of further functionalization derivatization. Preliminary mechanistic studies demonstrate that carbonyl oxygen possibly originates from corresponding alkene.

Language: Английский

Recent Advances in the Synthesis of 5‐MemberedN‐Heterocycles via Rhodium Catalysed Cascade Reactions DOI
Deepak Ranjan Mishra, Bhabani Shankar Panda, Sabita Nayak

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(22)

Published: June 9, 2022

Abstract Five membered N ‐heterocycles are significant targets in organic synthesis because of their ubiquitous existence bioactive natural products and pharmaceuticals. Over the past decade a compelling attractiveness has grown to develop rhodium complex catalysed efficient atom‐economic chemistry access structurally diverse ‐heterocyclic frameworks. This present review enlightens notable progresses advances 5‐membered via cascade reactions (annulations, C−H/C−C activation, cycloaddition, rearrangement, cyclization, metathesis) from 2018–2021.

Language: Английский

Citations

10

Directing group strategies in rhodium-catalyzed C–H amination DOI

Jiaoli Ma,

Xuming Zhou, Jialin Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(38), P. 7554 - 7576

Published: Jan. 1, 2022

With respect to the excellent catalytic performance, directing-group strategies in C–H amination catalyzed by rhodium are discussed relation types of aminating reagent, as well challenges and future development prospects.

Language: Английский

Citations

9

Asymmetric [5+1] Annulation via C–H Activation/1,4-Rh Migration/Double Bond Shift Using a Transformable Pyridazine Directing Group DOI

Man Zhu,

Yuyao Zhao,

Xingwei Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(11), P. 1839 - 1844

Published: March 13, 2023

N-Heterocycle-assisted C-H activation/annulation reactions have provided new concepts for the construction and transformation of azacycles. In this work, we disclose a [5+1] annulation reaction using novel transformable pyridazine directing group (DG). The DG-transformable mode led to heterocyclic ring accompanied by original via activation/1,4-Rh migration/double bond shift pathway, affording skeleton pyridazino[6,1-b]quinazolines with good substrate scope under mild conditions. Diverse fused cyclic compounds can be achieved derivatization product. asymmetric synthesis was also realized afford enantiomeric products stereoselectivity.

Language: Английский

Citations

5

Application of a transient directing strategy in cyclization reactionsviaC–H activation DOI
Ming Zhang,

Zukang Zhong,

Lihua Liao

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(14), P. 3882 - 3896

Published: Jan. 1, 2022

This review introduces seven types of cyclization reactions via C–H activation using a transient directing strategy.

Language: Английский

Citations

8

Tunable Rh(III)-Catalyzed C(sp2)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups DOI

E Junnan,

Luohe Wang,

Jing Zeng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7885 - 7890

Published: Sept. 6, 2024

A tunable Rh(III)-catalyzed C(sp

Language: Английский

Citations

1

Rhodium-catalyzed synthesis of N-substituted 3-acylpyrroles from enaminones and vinylene carbonate DOI
Jianbo Ma, Yiyong Yin,

Xing-Mei Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

We developed a cascade C–H activation/[3 + 2] annulation for enaminones and vinylene carbonate, employing the catalyst [Cp*RhCl 2 ] oxidants. This reaction allows efficient synthesis of 3-carbonylpyrroles.

Language: Английский

Citations

1

Regio- and Diastereoselective [3 + 2]-Spiroannulation of Benzoxazines with Chalcones: A Rh(III)-Catalyzed Redox-Neutral Approach to α-Aroyl Spiro-Indanamines DOI
Writhabrata Sarkar, Koushik Naskar, Shantonu Roy

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(15), P. 9988 - 10002

Published: July 13, 2022

We report an atom-economic Rh(III)-catalyzed [3 + 2]-spiroannulation reaction between cyclic ketimines and α,β-unsaturated carbonyl compounds, allowing the synthesis of novel spirocycles with concomitant generation three stereogenic centers in one pot. The does not require any silver additives or external oxidants is believed to proceed a redox-neutral manner. A broad substrate scope good functional group tolerance permitted vast spectrum spirocyclic 1,4-benzoxazine derivatives containing polysubstituted α-aroyl-indanamines excellent yields high diastereoselectivity.

Language: Английский

Citations

7

Free Amine-Directed Ru(II)-Catalyzed Redox-Neutral [4 + 2] C–H Activation/Annulation of Benzylamines with Sulfoxonium Ylides DOI
Yogesh N. Aher, Amit B. Pawar

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 12608 - 12621

Published: Sept. 9, 2022

An external oxidant free Ru(II)-catalyzed C–H functionalization/annulation of primary benzylamines with sulfoxonium ylides has been developed for the synthesis isoquinolines. The reaction utilizes amine as a directing group, which is generally considered to be poor group. This work presents first example Ru-catalyzed functionalization under redox-neutral conditions. detection amine-directed ruthenacyclic intermediate using high-resolution mass spectrometry corroborated involvement

Language: Английский

Citations

6

Rh(iii)-Catalyzed cascade annulation to produce an N-acetyl chain of spiropyrroloisoquinoline derivatives DOI
Yuan He, Jing Zheng, Lin Dong

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(11), P. 2293 - 2299

Published: Jan. 1, 2022

A new rhodium( iii )-catalyzed multistep cascade spirocyclization approach was developed to synthesize a novel N -acetyl chain of spiropyrroloisoquinoline derivatives using oxadiazoles as the directing group.

Language: Английский

Citations

5

Metal-/solvent-free oxidative [4 + 2]/[3 + 2] annulation of 2-ethynylbenzaldehydes with arylalkenes: facile synthesis of benzo[a]fluoren-5-ones DOI
Chengyong Wang, Jiang‐Xi Yu, Bang Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(11), P. 2939 - 2943

Published: Jan. 1, 2022

DTBP-mediated oxidative [4 + 2]/[3 2] annulation between 2-alkynylbenzaldehydes and arylalkenes toward benzo[ a ]fluoren-5-ones under metal-/solvent-free conditions is presented.

Language: Английский

Citations

5