Catalytic Aerobic Photooxidation of Phosphines using Four-Coordinated Orgnoboron Compounds as the Photocatalyst DOI
Liang Xu, Huanhuan Song,

Yingru Tang

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(14), P. 1698 - 1702

Published: Dec. 20, 2023

Abstract A photooxidation approach to the conversion of phosphines into corresponding phosphine oxides is reported. By taking advantage O2 in air as an oxidant and oxygen source, were obtained efficiently moderate excellent yields. four-coordinated organoboron compound was used photocatalyst activate its singlet state. This method features mild reaction conditions, broad functional-group tolerance, a wide substrate scope.

Language: Английский

Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System DOI
Jiawei Huang, Xiaoman Li, Liang Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 3054 - 3067

Published: Feb. 16, 2023

A three-component oxychalcogenation reaction, from alkenes, diselenides/thiophenols, and H2O/alcohols, has been realized herein. Tetrabutylammonium tribromide (TBATB) dimethylsulfoxide (DMSO) are utilized as the catalyst terminal oxidant, respectively, to enable this difunctionalization transformation. The metal-free reaction system shows good functional group compatibility, providing a unified practical approach access β-hydroxyl or β-alkoxy organochalcogenides.

Language: Английский

Citations

21
A visible-light-induced bromine radical initiates direct C–H alkylation of heteroaromatics DOI

Xiangxue Cao,

Lanfeng Wei,

Jinbo Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1157 - 1161

Published: Jan. 1, 2024

Herein, a photoinduced direct C(sp 2 )–H alkylation of N -heteroaromatics by using commercially available tetrabutylammonium tribromide (TBATB) as HAT reagent is described.

Language: Английский

Citations

4
Synthesis of β-Arylseleno Sulfoximines: A Metal-Free Three-Component Reaction Mediated by Tetrabutylammonium Tribromide DOI
Xiaoman Li, Jiawei Huang, Liang Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(16), P. 10684 - 10697

Published: Aug. 8, 2022

A tetrabutylammonium tribromide-mediated three-component reaction of alkenes, diselenides, and sulfoximines has been established herein, providing direct metal-free access to diverse β-arylseleno sulfoximine derivatives. This regioselective sulfoximido-selenization protocol proceeds efficiently under mild ambient conditions with generally good yields. strategy is featured by step atom economy, practicability, a broad substrate scope, gram-scale synthesis.

Language: Английский

Citations

16
Ni-Catalyzed Asymmetric C–P Cross-Coupling Reaction for the Synthesis of Chiral Heterocyclic Phosphine Oxides DOI

Ranran Cui,

Yinqi Wang,

Liyan Yuwen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(33), P. 6139 - 6142

Published: Aug. 11, 2023

Nickel performs excellently in C–C and C–X cross-coupling reactions. Here, we disclose a Ni(II)-catalyzed asymmetric C–P reaction to afford valuable chiral heterocyclic tertiary phosphine oxides. The method is mild efficient, which invokes self-sustained nickel catalytic cycle without an external reductant, light irradiation, or electricity.

Language: Английский

Citations

9
Selective Synthesis of Mono- and Bis-Phosphorylated (Dihydro)pyrans via TMSCl-Mediated Cascade Phosphorylation Cycloisomerization of Enynones DOI
Yi‐Feng Qiu, Qiang Wang,

Jian-He Cao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 26, 2024

A chlorotrimethylsilane (TMSCl)-mediated cascade phosphorylation and cycloisomerization of enynones with diphenylphosphine oxides is presented. This methodology enables the highly selective synthesis monophosphorylated 2

Language: Английский

Citations

3
Cobalt- or rhodium-catalyzed synthesis of 1,2-dihydrophosphete oxides via C–H activation and formal phosphoryl migration DOI Creative Commons
Shengbo Xu,

Ruijie Mi,

Guangfan Zheng

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 6012 - 6021

Published: Jan. 1, 2024

A highly stereo- and chemoselective intermolecular coupling of diverse heterocycles with dialkynylphosphine oxides has been realized

Language: Английский

Citations

2
Visible-Light-Induced C—C Bond Cleavage of Dihydroquinazolinones with Trifluoromethyl-Substituted Olefins Defluorinated Alkylation Reactions DOI Open Access

Xiangxue Cao,

Yahui Jia,

Shiji Yin

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1549 - 1549

Published: Jan. 1, 2024

The visible-light-induced C-C bond cleavage of dihydroquinazolinone to generate alkyl radicals for defluorinated alkylation reactions with α-trifluoromethyl alkene is reported.The method featured as transition-metal-free, mild conditions, base-or additive-free, and has a wide range substrate applicability, which provides convenient efficient new the synthesis various alkyl-substituted gem-difluoroalkene.

Language: Английский

Citations

2
Access to Polysubstituted Halophosphorylated Dihydrofurans via Halotrimethylsilane-Promoted Cascade Cyclization of γ-Hydroxyl Ynones with Diphenylphosphine Oxides DOI
Yi‐Feng Qiu, Shi‐Peng Chen,

Jian-He Cao

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(47), P. 8609 - 8614

Published: Nov. 20, 2022

A halotrimethylsilane (TMSX) accelerated cascade halophosphorylation and cycloisomerization of γ-hydroxyl ynones with diphenylphosphine oxides is presented. This methodology allows the one-step synthesis practical polysubstituted halophosphorylated dihydrofuran derivatives. It noteworthy that functions as a halogenation reagent well promoter to initiate this transformation. In addition, reaction system can also be scaled up gram quantities, produced halogenated compounds undergo further derivatizations by Pd-catalyzed coupling reactions.

Language: Английский

Citations

10
Visible light-induced metal-free chemoselective oxidative cleavage of benzyl C–heteroatom (N, S, Se) bonds utilizing organoboron photocatalysts DOI

Lanfeng Wei,

Wenbo Bai,

Zhiyan Hu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(89), P. 13344 - 13347

Published: Jan. 1, 2023

We have established a photooxidation system, which can realize formal carbonylation of C–heteroatom (N, S, Se) bonds.

Language: Английский

Citations

5
Visible Light-Mediated Organoboron-Catalyzed Metal-Free Synthesis of Silanols from Silanes DOI Creative Commons
Jinbo Yang,

Xiangxue Cao,

Lanfeng Wei

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(10), P. 4082 - 4082

Published: May 13, 2023

Herein, a four-coordinated organoboron compound, aminoquinoline diarylboron (AQDAB), is utilized as the photocatalyst in oxidation of silane to silanol. This strategy effectively oxidizes Si-H bonds, affording Si-O bonds. Generally, corresponding silanols can be obtained moderate good yields at room temperature under oxygen atmospheres, representing green protocol complement existing preparation methods for silanols.

Language: Английский

Citations

4