- Markovnikov-addition of H-phosphonates to terminal alkynes under metal- And solvent-free conditions
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An addition of H-phosphonates to aryl alkynes was realized under solvent- and metal-free conditions, affording Markovnikov-selective α-vinylphosphonates in moderate to good yields. A wide range of aryl alkynes could be applied for the reaction. A tentative mechanism of addition-substitution was proposed based onin situ31P {1H} NMR studies.
- Huang, Xian-Qiang,Lian, Yongjian,Lv, Yongzheng,Wang, Yongjie,Xin, Nana,Zhao, Chang-Qiu
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- Rhenium-Catalyzed Decarboxylative Tri-/Difluoromethylation of Styrenes with Fluorinated Carboxylic Acid-Derived Hypervalent Iodine Reagents
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Herein, unprecedented rhenium-catalyzed decarboxylative oxytri-/difluoromethylation and Heck-type trifluoromethylation of styrenes have been developed by using hypervalent iodine(III) reagents derived from cheap, stable, and easy-handling fluorinated carboxylic acids. Mechanistic studies revealed a radical decarboxylative trifluoromethylation pathway occurring in these reactions.
- Wang, Yin,Yang, Yunhui,Wang, Congyang
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supporting information
p. 1229 - 1233
(2019/11/21)
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- Pd-Catalysed Suzuki coupling of α-bromoethenylphosphonates with organotrifluoroborates: A general protocol for the synthesis of terminal α-substituted vinylphosphonates
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A general and robust protocol for the synthesis of terminal α-substituted vinylphosphonates via Suzuki coupling of α-bromovinylphosphonates with organotrifluoroborates has been successfully developed. This method features a broad substrate scope, great functional group compatibilities, and easy scale-up ability. In addition to easy access of nucleophiles, a straightforward synthesis of electrophiles was also realized with diethyl α-bromoethenylphosphonate as the starting material. With a combination of Pd2(dba)3/SPhos as the catalyst, a range of α-alkyl, aryl, heteroaryl, and alkynyl substituted ethenylphosphonates could be nicely accessed under mild conditions. As a synthetic application, the terminal vinylphosphonate was utilized as an effective Michael acceptor in the visible-light-promoted Giese reaction.
- Zhang, Li,Fang, Yewen,Jin, Xiaoping,Xu, Housan,Li, Ruifeng,Wu, Hao,Chen, Bin,Zhu, Yiming,Yang, Yi,Tian, Zongming
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supporting information
p. 8985 - 8989
(2017/11/09)
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- Pd-Catalyzed Synthesis of α-Aryl Vinylphosphonates via Suzuki Arylation of α-Phosphonovinyl Nonaflates
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The first palladium-catalyzed method for the arylation of α-phosphonovinyl nonaflates is described. Using a catalyst comprised of Pd(OAc)2 and SPhos, terminal and internal α-aryl vinylphosphonates could be efficiently accessed under mild condit
- Yuan, Meijuan,Fang, Yewen,Zhang, Li,Jin, Xiaoping,Tao, Minjia,Ye, Qilin,Li, Ruifeng,Li, Jinjian,Zheng, Hui,Gu, Juejun
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p. 1119 - 1123
(2015/11/02)
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- A simple and efficient method for one-pot, three-component synthesis of terminal vinylphosphonates using a task-specific ionic liquid
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A convenient and practical method for the one-pot, three-component synthesis of terminal vinylphosphonates from readily available starting materials (aryl/alkyl/heteroaryl aldehydes, nitromethane and trialkylphosphites) through a tandem Henry-Michael reaction followed by nitro elimination in the presence of 5-hydroxypentylammonium acetate (5-HPAA) as a task-specific ionic liquid, is described. This method offers several advantages such as the use of a reusable and inexpensive ionic liquid, which is an environmentally benign reaction medium, and a simple reaction setup that does not require specialized equipment. The approach offers good yields of the products under mild reaction conditions. Georg Thieme Verlag Stuttgart New York.
- Sobhani, Sara,Honarmand, Moones
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supporting information
p. 236 - 240
(2013/03/13)
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- Synthesis of vinylphosphonates and its first exploration of bioactivity
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Phosphonation of β-nitro-alkene with triethyl phosphite was achieved under microwave irradiation using CH2Cl2 as the solvent in the absence of catalyst with moderate to high yields (up to 90%). This method of formation of carbonphosphor bonds is simple, mild, convenient and effective. Synchronously, a number of vinylphosphonates derivatives were synthesized and evaluated biologically preliminary.
- Li, Sheng-Nan,Xu, Lan-Ting,Chenb, Yue,Lia, Ju-Lian,He, Ling
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experimental part
p. 416 - 422
(2012/05/04)
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- Enantioselective synthesis of chiral α-aryl or α-alkyl substituted ethylphosphonates via Rh-catalyzed asymmetric hydrogenation with a P-stereogenic BoPhoz-type ligand
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(Chemical Equation Presented) An enantioselective synthesis of optically active 1-aryl or 1-alkyl substituted ethylphosphonates, based on the first Rh-catalyzed asymmetric hydrogenation of corresponding α,β- unsaturated precursors with a P-stereogenic BoPhoz-type ligand under the mild condition, was developed, in which a wide range of 1-aryl or 1-alkyl substituted ethylphosphonates were achieved in up to 98% ee.
- Wang, Dao-Yong,Hu, Xiang-Ping,Deng, Jun,Yu, Sai-Bo,Duan, Zheng-Chao,Zheng, Zhuo
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supporting information; experimental part
p. 4408 - 4410
(2009/09/08)
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