Reactions of Ylides Generated from M C Bonds DOI

Shu-Sen Li,

Zihao Fu,

Jianbo Wang

et al.

Elsevier eBooks, Journal Year: 2021, Volume and Issue: unknown, P. 221 - 264

Published: Nov. 25, 2021

Language: Английский

Palladium-catalyzed diastereoselective synthesis of 2,2,3-trisubstituted dihydrobenzofurans via intramolecular trapping of O-ylides with activated alkenes DOI

Palagulla Maheswar Reddy,

Kuppan Ramachandran, Pazhamalai Anbarasan

et al.

Journal of Catalysis, Journal Year: 2021, Volume and Issue: 396, P. 291 - 296

Published: March 11, 2021

Language: Английский

Citations

13
Synthesis of Selenyl-Substituted Quinoline Derivatives via Substrate-Controlled Three-Component Domino Reactions DOI

Shuang-Shuang Sun,

Zu‐Yu Mo, Yanyan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(18), P. 12447 - 12454

Published: Sept. 1, 2022

A simple and efficient method for the preparation of selenyl-substituted quinoline derivatives through a CSp3–H selenylation in situ-generated 3-acetyl has been developed. This protocol is easy to handle, scalable, good functional group tolerant, providing rapid 3-selenoacetyl 3-diselenoacetyl derivatives.

Language: Английский

Citations

7
Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans DOI Open Access
Jagadeesh Kalepu, Bapurao Sudam Lad, Pratap Kumar Mandal

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

A new approach for the synthetically important γ-functionalized enals has been developed. The strategy involves rhodium-catalyzed direct C-C & C-S bond forming site-selective γ-difunctionalization of diazoenals with aryl propargyl sulfides via sulfur ylide [2,3] sigmatropic rearrangement, resulting in highly functionalized γ-allenyl(sulfanyl)enals excellent yield at ambient temperature. This versatile constitutes a viable alternative to remote carbonyl-directed γ-functionalization unmodified which suffer from competitive side reactions. synthetic utility was demonstrated by InCl

Language: Английский

Citations

1
Ru(II)-Catalyzed [1,4]-Sigmatropic Rearrangement and Intramolecular Concerted SNAr of Aryl and Heteroarylthio Derivatives using Quinoid Carbene DOI

Subarna Pan,

Md. Saimuddin Sk,

B. SANYAL

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18419 - 18428

Published: Dec. 2, 2024

A Ru(II)-catalyzed straightforward and efficient strategy has been developed to construct O-alkylated arylnaphthyl thioether derivatives using arylthioacetates/arylalkylthioethers with diazonaphthoquinone via a [1,4]-oxa sigmatropic rearrangement. In complementary method, heteroaryl thioacetate/heteroaryl alkylthioethers offer O-heteroaryl alkylnaphthyl an interesting concerted intramolecular SNAr-type reaction. Both of these methods proceed through the formation Ru-based quinoid carbene sulfur ylide, respectively. detailed mechanistic study DFT calculations reveal that reaction is going manner. Postsynthetic modifications synthesized compounds led sulfur-containing polyaromatic heterocycles.

Language: Английский

Citations

1
Rapid Photoracemization of Chiral Alkyl Aryl Sulfoxides DOI Creative Commons
Kosho Makino,

Kumi Tozawa,

Yuki Tanaka

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 17249 - 17256

Published: Nov. 20, 2021

The photoracemization of chiral alkyl aryl sulfoxides with a photosensitizer has not been sufficiently investigated thus far. Therefore, in this study, rapid reaction enantiopure using 1 mol % 2,4,6-triphenylpyrylium tetrafluoroborate (TPT+) was developed. Various substitution patterns were tolerated and every racemization proceeded extremely fast (k2 = 1.77 × 104-6.08 101 M-1 s-1, t1/2 0.4-114 s). Some easily oxidizable functional groups are appropriate for photoisomerization. electrochemical potentials the groups, determined via cyclic voltammetry, useful predicting reactive or nonreactive reaction. A theoretical study conducted to clarify sp2-like nature S sulfoxide cation radical, which makes easier.

Language: Английский

Citations

7
Metal-Bound or Free Ylides as Reaction Intermediates in Metal-Catalyzed [2,3]-Sigmatropic Rearrangements? It Depends. DOI Creative Commons
Croix J. Laconsay, Dean J. Tantillo

Published: Nov. 3, 2020

Density functional theory calculations were applied to study four previously published metal-catalyzed [2,3]-rearrangements from onium ylide intermediates, in pursuit of generalizations about when, during these types reactions, catalysts dissociate. Our results corroborate past studies where free mechanisms proposed be operative. Calculations on case predict that the origin metal-catalyst ‘falling off’ (dissociation) can attributed primarily steric bulkiness groups adjacent carbene carbon.

Language: Английский

Citations

6
Rh(II) catalyzed efficient sigmatropic rearrangement reaction of pyridotriazoles and sulfides DOI Creative Commons
Yuting Chen,

Guanghui Lv,

Zhiyang Li

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: 5(2), P. 77 - 79

Published: April 23, 2023

The [2,3]- and [1,2]-sigmatropic rearrangement reactions between pyridotriazoles sulfides catalyzed by rhodium(II) were investigated. utilization of as the carbene precursors in this kind reaction efficiently constructed C(sp3)-S C(sp3)-Se bond with broad substrate scope great functional group tolerance.

Language: Английский

Citations

2
Sulfoxonium Ylides as Carbene Precursors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds DOI

Cankun Luo,

Zhiqian Lin,

Yingdi Hao

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(43)

Published: Aug. 30, 2023

Abstract Rhodium‐catalyzed Sommelet‐Hauser rearrangement derived from α‐thioesters/α‐selenoesters and sulfoxonium ylides has been developed for the synthesis of various sulfur/selenium‐containing ortho‐substituted aromatic compounds in medium to excellent yields (39 examples; up 97 %). Sulfoxonium as safe carbene precursors are firstly used reactions, which is superior traditional diazo compounds. The present reaction advantages mild condition, safety broad substrate scope, afford a unique method with tertiary carbon center.

Language: Английский

Citations

2
A copper-catalyzed three-component reaction of dithioacetals with diazo ketones and ketimines DOI
Hongkai Sha, Yu Qian,

Xiangji Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(42), P. 8223 - 8227

Published: Jan. 1, 2022

A copper-catalyzed three-component reaction of dithioacetals with diazo-ketones and ketimines has been reported. This proceeds via trapping the highly active sulfur ylide species, which are generated from thioacetal carbene intermediates, isatin-derived ketimine, providing an efficient protocol for synthesis acyclic derivatives medium-sized sulfur-containing heterocycles in good to high yields under mild conditions a broad substrate scope.

Language: Английский

Citations

2
New Catalysts for Asymmetric Oxidation of Prochiral Sulfides Based on Vanadium Complexes with Levopimaric Acid Derivatives DOI

V. N. Konev,

Ilia V. Eltsov, З. П. Пай

et al.

Kinetics and Catalysis, Journal Year: 2022, Volume and Issue: 63(6), P. 676 - 686

Published: Dec. 1, 2022

Language: Английский

Citations

1