Crystal structure of 1-(4-bromophenyl)but-3-yn-1-one DOI Creative Commons

Shaziyaparveen K. Siddiqui,

Chepuri V. Ramana, Rajesh G. Gonnade

et al.

Acta Crystallographica Section E Crystallographic Communications, Journal Year: 2023, Volume and Issue: 79(7), P. 633 - 636

Published: June 13, 2023

The title compound, 1-(4-bromo-phen-yl)but-3-yn-1-one, C10H7BrO, crystallizes in the monoclinic space group P21/n with one mol-ecule asymmetric unit. structure displays a planar geometry. crystal is consolidated by C-H⋯O hydrogen bonding and short C=O⋯C≡C (acetyl-ene) contacts. Hirshfeld surface analysis indicates that H⋯H, C⋯H/H⋯C H⋯Br/Br⋯H inter-actions play more important role consolidating compared to H⋯O/O⋯H C⋯C

Language: Английский

Hydroxyl-Directed Ru(II)-Catalyzed Synthesis of Fused Dihydrofurans Using 1,4-Dioxane and Sulfoxonium Ylides as Annulating Agents DOI

Jyotshna Phukon,

Pratiksha Bhorali,

Sumi Changmai

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(1), P. 215 - 219

Published: Jan. 3, 2023

An unprecedented annulation reaction is developed for the synthesis of dihydrofuran-fused compounds. In this Ru-catalyzed hydroxyl-group-directed reaction, easily affordable sulfoxonium ylides and 1,4-dioxane were used as annulating partners. This first example use a methylene source to construct heterocyclic scaffold. A wide range dihydrofuran0fused coumarins naphthalenes synthesized using three-component reaction.

Language: Английский

Citations

19

Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate DOI

Jia‐Lin Song,

Lin Xiao,

Shaoyong Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1457 - 1464

Published: April 14, 2023

Abstract In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides N ‐carbamoylindoles with carbonate was accomplished, which afforded a series naphthalenones containing β‐ketosulfoxonium ylide moiety, isocoumarins, pyrimidones. This protocol featured mild conditions, broad substrate scope, functional‐groups compatibility. addition, related applications preliminary mechanistic exploratory were also investigated magnified image

Language: Английский

Citations

14

Copper-Mediated Cyclization of Terminal Alkynes with CF3-Imidoyl Sulfoxonium Ylides To Construct 5-Trifluoromethylpyrroles DOI
Magdy I. El‐Zahar, Zhou Li,

Yixin Tong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2249 - 2254

Published: March 7, 2024

A copper-mediated [3 + 2] cyclization of CF3-imidoyl sulfoxonium ylides and terminal alkynes has been demonstrated. This work provides a practical approach for assembling 5-trifluoromethylpyrroles with the merits broad substrate scope, good functional tolerance, mild reaction conditions. Control experiments DFT studies indicate that this may involve addition π-bonds by copper-carbene radicals hydrogen migration.

Language: Английский

Citations

6

Transition metal-catalyzed C–H/C–C activation and coupling with 1,3-diyne DOI
Bedadyuti Vedvyas Pati,

Nitha Nahan Puthalath,

Shyam Kumar Banjare

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(14), P. 2842 - 2869

Published: Jan. 1, 2023

The 1,3-diynes hold a prominent position among the many coupling partners employed in metal-catalysed C–H activation because of their ability to form complex bis-heterocycles one shot.

Language: Английский

Citations

12

Cascade C–H Activation/Annulation of Sulfoxonium Ylides with Vinyl Cyclopropanes: Access to Cyclopropane-Fused α-Tetralones DOI
Sharajit Saha, Bijoy Debnath, Kangkan Talukdar

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3352 - 3357

Published: May 4, 2023

Rh-catalyzed weak and traceless directing-group-assisted cascade C–H activation annulation of sulfoxonium ylides with vinyl cyclopropanes as a coupling partner have been accomplished to furnish functionalized cyclopropane-fused tetralones at moderate temperature. The C–C bond formation, cyclopropanation, functional group tolerance, late-stage diversifications drug molecules, scale-up are the important practical features.

Language: Английский

Citations

12

Ru(II)-Catalyzed C–H Functionalization of 2-Arylbenzimidazoles with Iodonium Ylides: A Straightforward Access to Bridgehead Polycyclic N-Heterocycles DOI
Saiprasad Nunewar, Sanjeev Kumar,

Akhilesh Waman Meshram

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 13757 - 13762

Published: Oct. 25, 2022

Herein, we disclose an efficient ruthenium-catalyzed C–H functionalization of 2-arylbenzimidazoles/2-arylimidazoles with iodonium ylides leading to substituted tetracyclic and pentacyclic bridgehead N-heterocycles, wherein ylide acts as a carbene precursor. For the first time, proceeds through Ru–carbenoid intermediate. Further, synthetic utility this protocol was successfully shown for gram-scale synthesis useful transformations.

Language: Английский

Citations

18

Palladium Catalyzed Dicarbonylation of α-Iodo-Substituted Alkylidenecyclopropanes: Synthesis of Carbamoyl Substituted Indenones DOI
Lin Li,

Xin‐Lian Liu,

Jin-Yan Liang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(30), P. 5624 - 5628

Published: July 27, 2022

A palladium catalyzed dicarbonylation of α-iodo-substituted ACPs for the synthesis carbamoyl substituted indenones has been developed. Two carbonyl groups were incorporated into product with cleavage proximal C-C bond ACPs. broad range efficiently prepared in good to excellent yields.

Language: Английский

Citations

16

[Cp*IrCl2]2-Catalyzed Amidocarbonation of Olefins with Sulfoxonium Ylides toward Functionalized Isoindolin-1-ones DOI
Qi Yang,

Junxue Bai,

Han Yang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7148 - 7153

Published: Sept. 26, 2023

A [Cp*IrCl2]2-catalyzed amidocarbonation of olefins with sulfoxonium ylides has been developed to generate diverse biologically important isoindolin-1-ones in high efficiency under mild reaction conditions. Mechanism studies indicated that this cascade was triggered by amino-iridation the olefin unit iridacycle, followed formal migratory insertion ylides. This newly method features broad substrate scopes and operational simplicity.

Language: Английский

Citations

9

Rh(III)-catalyzed C–H/C–C activation of benzoylacetonitriles and cyclization with CF3-imidoyl sulfoxonium ylides to 3-trifluoromethyl-isoquinolones DOI

Zuguang Yang,

Pinyi Li,

Zhengkai Chen

et al.

Journal of Catalysis, Journal Year: 2023, Volume and Issue: 427, P. 115098 - 115098

Published: Aug. 19, 2023

Language: Английский

Citations

8

Palladium(II)-Catalyzed Intramolecular [2 + 2 + 2] Annulation of Indolyl 1,3-Diynes: Construction of Azepino-Fused Carbazoles DOI

Meng-Lian Yao,

Xiaoyuan Wang,

Guang-Chao Feng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(25), P. 4615 - 4620

Published: June 21, 2023

A novel palladium(II)-catalyzed intramolecular [2 + 2 2] annulation of indolyl 1,3-diynes is described in this contribution. variety azepino-fused carbazoles are obtained moderate to excellent yields. The key the success transformation use a carboxylic acid as an additive. This protocol features broad functional group tolerances, easy handling air, and 100% atom economy. Furthermore, scale-up reactions, late-stage derivatizations, photophysical property investigations highlight potential synthetic utility methodology.

Language: Английский

Citations

8