78375-70-9Relevant articles and documents
Cobalt(II)-Catalyzed Bisfunctionalization of Alkenes with Diarylphosphine Oxide and Peroxide
Shen, Jian,Xiao, Bo,Hou, Yang,Wang, Xue,Li, Gui-Zhi,Chen, Jin-Chun,Wang, Wei-Li,Cheng, Jian-Bo,Yang, Bin,Yang, Shang-Dong
, p. 5198 - 5209 (2019)
The low-cost cobalt(II) catalyst has been used for the first time to achieve P(O)-radical-mediated bisfunctionalization of alkenes with diarylphosphine oxide and peroxides. This simple process is performed under mild conditions to afford a wide variety of phosphonation-peroxidation products in a one-pot manner. Computational studies are carried out to provide a theoretical support for the P(O)-radical-involved bisfunctionalization of alkenes. (Figure presented.).
Phosphinoyl Radical-Initiated 1,2-Bifunctional Thiocyanodiphenylphosphinoylation of Alkenes
Tao, Ze-Kun,Li, Cheng-Kun,Zhang, Pei-Zhi,Shoberu, Adedamola,Zou, Jian-Ping,Zhang, Wei
, p. 2418 - 2424 (2018)
1,2-Bifuctional thiocyanodiphenylphosphinoylation of alkenes is established through the phosphinoyl radical addition followed by Cu-catalyzed thiocyanation. This one-pot reaction is applicable to a range of aromatic, aliphatic, and cyclic alkenes to afford thiocyanodiphenylphosphinoylated compounds in satisfactory yields.
Visible-Light-Promoted Aerobic Oxyphosphorylation of α-Diazoesters with H-Phosphine Oxides
Wang, Cunhui,Wang, Ganggang,Yang, Jingya,Zhou, Hongyan
, (2022/03/01)
A visible-light-promoted aerobic oxyphosphorylation of α-diazoesters and H-phosphine oxides has been developed. Using air as the oxygen source, the reaction proceeded smoothly at room temperature under blue-light irradiation. The α-diazoesters, molecular oxygen, and H-phosphine oxides are conveniently incorporated into a C-O-P(O) unit in one step. The preliminary mechanistic studies indicated that a light-triggered radical process is involved. The developed strategy shows the unrevealed reactivity of diazo compounds with H-phosphine oxides and has potential value in synthetic applications.
Photoinduced Phosphorylation/Cyclization of Cyanoaromatics for Divergent Access to Mono- And Diphosphorylated Polyheterocycles
Shi, Shanshan,Zheng, Zhipeng,Zhang, Yumeng,Yang, Yufei,Ma, Denghui,Gao, Yuzhen,Liu, Yan,Tang, Guo,Zhao, Yufen
supporting information, p. 9348 - 9352 (2021/12/14)
The visible-light-driven switchable phosphorylation of cyanoaromatics with the 1,6-enyne moiety for the diverse and selective synthesis of phosphorylated polyheterocycles, including phosphorylated aminophosphonates, iminophosphonates, and ketones, has bee
Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes
Bian, Xue-Wei,Zhang, Ling,Shoberu, Adedamola,Zou, Jian-Ping
, (2021/04/02)
A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.
Visible light induced radical cascade cyclization of: Ortho -cyanoarylacrylamides with phosphine oxides for the preparation of phosphorylated quinoline-2,4(1 H,3 H)-dione
Han, Qing-Qing,Song, Jing-Cheng,Sun, Yuan-Yuan,Wang, Zu-Li,Yang, Shao-Hui,Yue, Shan,Zhang, En-Xuan
, p. 16438 - 16441 (2021/10/01)
Visible light induced cascade cyclization of ortho-cyanoarylacrylamides with phosphine oxides for the preparation of phosphorylated quinoline-2,4(1H,3H)-dione. Products with moderate to good yields were efficiently isolated. A radical mechanism was propos
Palladium-Catalyzed Olefination of N-Tosylhydrazones as β-Diazo Phosphonate Precursors with Arylhalides
He, Jing,Feng, Yijiao,Yang, Fang,Dai, Bin,Liu, Ping
supporting information, p. 5857 - 5861 (2020/09/21)
An efficient palladium-catalyzed olefination of N-tosylhydrazones as β-diazo phosphonate precursors with aryl halides has been developed. 2,2-Disubstituted vinylphosphonates bearing versatile functional groups were easily accessed in moderate to excellent
Electrochemical Oxidative Phosphorylation of Aldehyde Hydrazones
Li, Yueheng,Mo, Guangquan,Ruan, Zhixiong,Sun, Ping-Hua,Xu, Zhongnan,Zeng, Shaogao,Zheng, Yucheng
supporting information, p. 4016 - 4020 (2020/07/14)
The electrochemical phosphorylation of aldehyde hydrazones has been developed under exogenous oxidant-free conditions. The strategy provides expedient access to highly functionalized α-iminophosphine oxides with ample scope and broad functional group tole
Cobaloxime Catalysis: selective synthesis of alkenylphosphine oxides under visible light
Liu, Wen-Qiang,Lei, Tao,Zhou, Shuai,Yang, Xiu-Long,Li, Jian,Chen, Bin,Sivaguru, Jayaraman,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 13941 - 13947 (2019/09/30)
Direct activation of H-phosphine oxide to react with an unsaturated carbon-carbon bond is a straightforward approach for accessing alkenylphosphine oxides, which shows significant applications in both synthetic and material fields. However, expensive metals and strong oxidants are typically required to realize the transformation. Here, we demonstrate the utility of earth-abundant cobaloxime to convert H-phosphine oxide into its reactive radical species under visible light irradiation. The radical species thus generated can be utilized to functionalize alkenes and alkynes without any external photosensitizer and oxidant. The coupling with terminal alkene generates E-alkenylphosphine oxide with excellent chemo- A nd stereoselectivity. The reaction with terminal alkyne yields linear E-alkenylphosphine oxide via neutral radical addition, while addition with internal ones generates cyclic benzophosphine oxides and hydrogen. Mechanistic studies on radical trapping experiments, electron spin resonance studies, and spectroscopic measurements confirm the formation of phosphinoyl radical and cobalt intermediates that are from capturing the electron and proton eliminated from H-phosphine oxide. The highlight of our mechanistic investigation is the dual role played by cobaloxime, viz., both as the visible light absorber to activate the P(O)-H bond as well as a hydrogen transfer agent to influence the reaction pathway. This synergetic feature of the cobaloxime catalyst preforming multiple functions under ambient condition provides a convergent synthetic approach to vinylphosphine oxides directly from H-phosphine oxides and alkenes (or alkynes).
Cobaloxime Catalysis: Selective Synthesis of Alkenylphosphine Oxides under Visible Light
Liu, Wen-Qiang,Lei, Tao,Zhou, Shuai,Yang, Xiu-Long,Li, Jian,Chen, Bin,Sivaguru, Jayaraman,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 13941 - 13947 (2019/09/30)
Direct activation of H-phosphine oxide to react with an unsaturated carbon-carbon bond is a straightforward approach for accessing alkenylphosphine oxides, which shows significant applications in both synthetic and material fields. However, expensive metals and strong oxidants are typically required to realize the transformation. Here, we demonstrate the utility of earth-abundant cobaloxime to convert H-phosphine oxide into its reactive radical species under visible light irradiation. The radical species thus generated can be utilized to functionalize alkenes and alkynes without any external photosensitizer and oxidant. The coupling with terminal alkene generates E-alkenylphosphine oxide with excellent chemo- and stereoselectivity. The reaction with terminal alkyne yields linear E-alkenylphosphine oxide via neutral radical addition, while addition with internal ones generates cyclic benzophosphine oxides and hydrogen. Mechanistic studies on radical trapping experiments, electron spin resonance studies, and spectroscopic measurements confirm the formation of phosphinoyl radical and cobalt intermediates that are from capturing the electron and proton eliminated from H-phosphine oxide. The highlight of our mechanistic investigation is the dual role played by cobaloxime, viz., both as the visible light absorber to activate the P(O)-H bond as well as a hydrogen transfer agent to influence the reaction pathway. This synergetic feature of the cobaloxime catalyst preforming multiple functions under ambient condition provides a convergent synthetic approach to vinylphosphine oxides directly from H-phosphine oxides and alkenes (or alkynes).
