Paper
Rh(III)-Catalyzed Diastereoselective Annulation of Amides with Quinone Monoacetals: Access to Bridged Nine-Membered Heterocycles via C-H Activation.
Published Jan 19, 2017 · Wei Yang, Jinhuan Dong, Jingyi Wang
Organic letters
Q1 SJR score
30
Citations
0
Influential Citations
Abstract
An unprecedented Rh(III)-catalyzed annulation of various benzamides and acrylamides with quinone monoacetals was developed for the facile and efficient one-pot synthesis of bridged nine-membered benzo[c]azonine-1,5(2H)-diones and 2-azabicyclo[4.3.1]dec-4-ene-3,8-diones. It is the first example of synthesis of nine-membered heterocycles through Rh(III)-catalyzed C-H bond functionalization, and both aryl and vinyl C-H bonds are tolerant in this reaction. A plausible mechanism is proposed on the basis of control experiments.
Study Snapshot
Rh(III)-catalyzed annulation of benzamides and acrylamides with quinone monoacetals allows for facile and efficient one-pot synthesis of bridged nine-membered heterocycles, with both aryl and vinyl C-H bonds being tolerant.
PopulationOlder adults (50-71 years)
Sample size24
MethodsObservational
OutcomesBody Mass Index projections
ResultsSocial networks mitigate obesity in older groups.
Full text analysis coming soon...
References
A Simple and Versatile Amide Directing Group for C-H Functionalizations.
The N-methoxy amide (CONHOMe) moiety is a simple and versatile directing group for C-H activation transformations in Pd(II), Rh(III), and Ru(II) catalysts, enabling a wide range of C-H activation transformations.
2016·457citations·Ru-Yi Zhu et al.·Angewandte Chemie
Angewandte Chemie
Kinetic Control of Rh(III)-Catalyzed Annulation of C-H Bonds with Quinones: Chemoselective Synthesis of Hydrophenanthridinones and Phenanthridinones.
This Rh(III)-catalyzed C-H bond annulation process allows for the chemoselective synthesis of hydrophenanthridinones and phenanthridinones at room temperature, with temperature-dependent control.
2016·37citations·Wei Yang et al.·The Journal of organic chemistry
The Journal of organic chemistry
A [4+1] Cyclative Capture Approach to 3H-Indole-N-oxides at Room Temperature by Rhodium(III)-Catalyzed CH Activation.
Rhodium(III)-catalyzed [4+1] CH oxidative cyclization of nitrones with diazo compounds allows for the synthesis of pharmaceutically important N-hydroxyindoles and 3H-indole-N-oxides at room temperature.
2015·103citations·Yaxi Yang et al.·Angewandte Chemie
Angewandte Chemie
All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C–H Functionalization and 1,4-Migration
Rhodium(III)-catalyzed, all-carbon [3+3] oxidative annulations of 1,3-enynes produce spirodialins through alkenyl-to-allyl 1,4-rhodium(III) migration.
2015·61citations·David J. Burns et al.·Angewandte Chemie (International Ed. in English)
Angewandte Chemie (International Ed. in English)
Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)-H Functionalization.
Rhodium(III)-catalyzed [3+2]/[5+2] annulation of 4-aryl 1,2,3-triazoles with internal alkynes provides straightforward access to indeno[1,7-cd]azepine architectures.
2015·119citations·Yuan-Liang Yang et al.·Angewandte Chemie
Angewandte Chemie
Citations
A Regioselective, One-Pot, Transition-Metal-Free α-Alkylation of Quinone Monoacetals for Various Organic Transformations.
This study presents a regioselective, one-pot, transition-metal-free -alkylation of quinone monoacetals for various organic transformations, with potential applications in biomedicine.
2024·0citations·Pragya Sharma et al.·Organic letters
Organic letters
Rh(III)-Catalyzed C-H Activation/Annulation for the Construction of Quinolizinones and Indolizines.
Rh(III)-catalyzed C-H activation/anulation effectively creates biologically active quinolizinone and indolizine derivatives from readily available enamide and triazole substrates.
2024·1citation·Xinjiao Hou et al.·Organic letters
Organic letters
Anion Cascade Reactions. Part I: Synthesis of 3-Isoquinuclidones from a Nazarov-like Reagent.
This study presents a simple, atom-economical one-step protocol for the synthesis of biologically valuable 3-isoquinuclidones using a Nazarov-like reagent and intramolecular hemiamination under mild conditions.
2023·1citation·Mengjuan Li et al.·Organic letters
Organic letters
Rh(III)-Catalyzed annulative aldehydic C-H functionalization for accessing ring-fluorinated benzo[b]azepin-5-ones
Rh(III)-catalyzed annulative aldehydic C-H functionalization allows for the production of new ring-fluorinated benzo[b]azepin-5-ones with high regioselectivity and good yields.
2022·14citations·Qiuyun Li et al.·Chinese Chemical Letters
Chinese Chemical Letters
Rh(iii)-catalyzed synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones via C–H activation and C–C bond cleavage
Rh(iii)-catalyzed redox-neutral synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones enables a novel -C elimination step.
2022·16citations·Wei Yang et al.·RSC Advances
RSC Advances
Cp*Co(III)-catalyzed C-H amination/annulation cascade of sulfoxonium ylides with anthranils for the synthesis of indoloindolones.
The Cp*Co(III)-catalyzed C-H amination/annulation cascade effectively synthesizes indole-indolone scaffolds, utilizing the dual functionality of anthranils for nitrogen and aldehyde groups.
2021·3citations·Yogesh N Aher et al.·Chemical communications
Chemical communications
20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions
Acrylamides are efficient domino partners for forming complex aza-heterocycles through metal-free and metal-triggered reactions, allowing for modulation of acrylamide reactivity.
2021·7citations·Ismail Alahyen et al.·Synthesis
Synthesis
Recent Achievements in the Rhodium‐Catalyzed Concise Construction of Medium N‐Heterocycles, Azepines and Azocines
Rhodium catalysis has enabled rapid access to 7 and 8-membered N-heterocycles, enabling new drug discovery based on these compounds.
2020·25citations·Wensen Ouyang et al.·Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis