Synthesis of 2,4-Disubstituted Oxazoles by a Copper-Catalyzed [3+2] Annulation/Olefination Cascade between Amides and IIII/PV Hybrid Ylides DOI
Zhaofeng Wang, Xingchen Ye

Synlett, Journal Year: 2023, Volume and Issue: 35(10), P. 1153 - 1159

Published: Oct. 2, 2023

Abstract We report a novel and efficient method for oxazole synthesis through copper-catalyzed [3+2] annulation/olefination cascade between readily available iodonium–phosphonium hybrid ylides amides. An unprecedented α-phosphonium Cu carbenoid acts as the key intermediate. This features excellent regioselectivity with mild reaction conditions broad substrate scope. Its synthetic utility is demonstrated by its application in late-stage functionalizations rapid of chiral ligand based on an motif.

Language: Английский

Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy DOI

Mingxuan Liang,

Mengling He,

Zhiqing Zhong

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(17)

Published: Feb. 22, 2024

Abstract To date, it remains challenging to achieve a general and catalytic α‐arylation of cyclic 1,3‐dicarbonyls, particularly ubiquitous heteroaromatic ones. In most cases, the preparation their medically significant arylated derivatives requires multistep synthetic sequences. Herein, we introduce new, convenient strategy involving conversion 1,3‐dicarbonyls iodonium ylides ( CIY s), followed by rhodium‐catalyzed with arylboronic reagents via carbene coupling. This approach is mild, operationally simple, base‐free, biocompatible, exhibits broad substrate scope (>100 examples), especially respect various ortho ‐substituted or base‐sensitive acids. Importantly, owing excellent compatibility acids boronate esters (ArBpin, ArBneop, ArBF 3 K), this method allows late‐stage installation heterocyclic 1,3‐dicarbonyl motifs in highly complex settings. The utility transformation further demonstrated through significantly simplifying synthesis several bioactive molecules natural products.

Language: Английский

Citations

10
Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C–H Activation/[4+2] Cyclization DOI
Xueqing Liu,

Sijia Shi,

Wenqian Ding

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5136 - 5140

Published: June 7, 2024

Herein, we report a rhodium-catalyzed C–H activation/[4+2] cyclization reaction between α,β-unsaturated amides and iodonium ylides for the synthesis of novel 7,8-dihydroquinoline-2,5-diones analogues. This protocol provides series pyridones fused with saturated cycles good functional group compatibility, water air tolerance, to excellent yields under mild green conditions. Additionally, scale-up can be smoothly performed as low 0.25 mol % catalyst loading. Recycling experiments different transformation were also carried out demonstrate potential synthetic utility this protocol.

Language: Английский

Citations

8
Rhodium(III)‐Catalyzed Divergent C−H Functionalization of N‐Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts DOI
Jie Ren, Yang Liu, Chao Pi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1817 - 1823

Published: Feb. 7, 2023

Abstract We described an Rhodium(III)‐catalyzed divergent C−H bond functionalization of N ‐aryl amidines with iodonium ylides. Carbazolones and zwitterionic salts were diversely constructed through intermolecular annulation intramolecular proton transfer under the different reaction conditions. This protocol is operationally simple tolerates a variety functional groups. The efficient post‐modification pharmaceutical molecules demonstrates its practicability.

Language: Английский

Citations

19
Rh-Catalyzed C–H Activation/Annulation of Enaminones and Cyclic 1,3-Dicarbonyl Compounds: An Access to Isocoumarins DOI
Qian Wang, Ying Li,

Jina Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5348 - 5358

Published: April 3, 2023

A facile access to isocoumarins has been established via rhodium(III)-catalyzed C-H bond activation and intramolecular C-C cascade annulation of enaminones cyclic 1,3-dicarbonyl compounds. The synthetic protocol features a wide range substrates with high functional group tolerance, mild reaction conditions, the selective cleavage enaminone bond. Notably, compounds can in situ-generate iodonium ylide as carbene precursor prepare polycyclic scaffolds by reacting PhI(OAc)2. application this method useful precursors bioactive skeletons is also exemplified.

Language: Английский

Citations

18
Rhodium-Catalyzed Difunctionalization of Alkenes Using Cyclic 1,3-Dicarbonyl-Derived Iodonium Ylides DOI
Zhenwei Zhang,

Borong Su,

Jiajun Gong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1886 - 1890

Published: Feb. 28, 2024

Herein, we introduce an iodonium ylide strategy to achieve novel α-alkylation of cyclic 1,3-dicarbonyls through harnessing C(sp3)–Rh species generated from 5-exo-trig cyclization provide rapid access molecular hybridization medically important isoindolin-1-ones and readily available substrates. This approach features mild conditions, good yield, excellent functional group tolerance, the simultaneous formation two new chemical bonds one stereogenic center. Moreover, hydroxyl resulting product provides a handle for downstream transformations. Importantly, also demonstrate this can be achieved in one-pot manner. A complex was prepared proved key intermediate.

Language: Английский

Citations

8
Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes DOI
Xiao Liu, Bingxin Zhou, Kelu Yan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1744 - 1750

Published: Feb. 22, 2024

Abstract The transmetalation triggered rhodium‐catalyzed C−H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium has been developed. Various products phenanthrenes were constructed under redox‐neutral conditions in 34–86% yields. Several mechanism exploration experiments derivatization reactions conducted sequence to gain a deeper understanding the process potential this transformation. It offers an alternative approach for synthesis phenanthrene derivatives.

Language: Английский

Citations

6
Modern photo- and electrochemical approaches to aryl radical generation DOI Creative Commons

Krzysztof Grudzień,

Andrei Zlobin,

Jan Zadworny

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5232 - 5277

Published: Jan. 1, 2024

This review describes recent advances in the generation of aryl radicals using light and electricity. Such modern techniques allow for efficient energy resource utilization, thus providing more sustainable radical arylation methods.

Language: Английский

Citations

6
Visible-Light-Induced Annulation of Iodonium Ylides and 2-Isocyanobiaryls to Access 6-Arylated Phenanthridines DOI
Jinyang Chen, Hongyu Wu,

Hai‐Yang Song

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8360 - 8368

Published: June 1, 2023

A 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN)-photocatalyzed cascade arylation/cyclization reaction of 2-isocyanobiaryls and iodonium ylides was established for the synthesis 6-arylated phenanthridines. This is first example employing as aryl radical sources in a visible-light-induced cyclization reaction.

Language: Английский

Citations

13
Rh-Catalyzed α-Arylation of Cyclic 1,3-Dicarbonyls with Benzocyclobutenols Enabled by a Cyclic Iodonium Ylide Strategy DOI

Borong Su,

Zhenwei Zhang, Shangkun Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4383 - 4387

Published: May 14, 2024

To date, the general and catalytic α-arylation of cyclic 1,3-dicarbonyls remains elusive. We now report first Rh-catalyzed with benzocyclobutenols through a iodonium ylide strategy. Our strategy represents good solution for previously challenging sterically demanding aryl partners, which is especially appropriate structurally unique heteroaromatic 1,3-dicarbonyls. approach features mild conditions, readily available starting materials, high yields, excellent functional group-tolerance, simple operation, providing expedient access toward medically important 2-aryl (hetero)cyclic The practicality this demonstrated by gram-scale synthesis, one-pot numerous downstream transformations.

Language: Английский

Citations

5
Rh(iii)-catalyzed C(sp2)–H functionalization/[4+2] annulation of oxadiazolones with iodonium ylides to access diverse fused-isoquinolines and fused-pyridines DOI

Wang-Liang Chen,

Jia‐Lin Song,

Sheng Fang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6560 - 6563

Published: Jan. 1, 2024

A Rh( iii )-catalyzed C–H/N–H [4+2] annulation of oxadiazolones with iodonium ylides was developed, which afforded a series fused-isoquinolines and fused-pyridines.

Language: Английский

Citations

4