16965-72-3Relevant academic research and scientific papers
Rh(I)-Catalyzed Arylation of α-Diazo Phosphonates with Aryl Boronic Acids: Synthesis of Diarylmethylphosphonates
Zhou, Yujing,Zhang, Yan,Wang, Jianbo
, p. 621 - 627 (2017)
An efficient synthetic method for diarylmethylphosphonates is presented. A series of phosphonate derivatives with diverse functional groups can be accessed via a rhodium catalyzed cross-coupling reaction between α-diazo phosphonates and aryl boronic acids. Migratory insertion of rhodium carbene intermediates is postulated to be the critical step in this transformation.
Synthesis of α-Aryldiazophosphonates via a Diazo Transfer Reaction
Beletskaya, Irina P.,Titanyuk, Igor D.
, p. 2748 - 2757 (2022/03/14)
The simple synthetic procedure for preparation of α-aryl-α-diazophosphonates via a diazo transfer reaction is proposed. Benzylphosphonates reacted with tosyl azide (TsN3) in the presence of potassium tert-butoxide (KOtBu) to afford diazophosphonates in a yield up to 79%. The proposed method is general. The reaction uses easily available starting materials, tolerates various functional groups, and may be applied for multi-gram scale synthesis.
N-transfer reagent and method for preparing the same and its application
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Page/Page column 26-29; 59-60; 69-70; 77-78, (2021/06/25)
Provided are a novel N-transfer reagent and a method for preparing the same and its application. The N-transfer reagent is represented by the following Formula (I): The various novel N-transfer reagents of the present invention can be quickly prepared by employing different nitrobenzene precursors. The N-transfer reagents can directly convert a variety of amino compounds into diazo compounds under mild conditions. Particularly, the N-transfer reagents can facilitate the synthesis of the diazo compounds. The application of synthesizing diazo compounds of the present invention can greatly decrease the difficulty in operation, increase the safety during experiments, reduce the cost of production and the environmental pollution, and enhance the industrial value of diazo compounds.
A removable functional group strategy for regiodivergent Wittig rearrangement products
Alam, Md Nirshad,Lakshmi,Maity, Pradip
supporting information, p. 8922 - 8926 (2018/12/10)
[1,2] and [2,3] Wittig rearrangements are competing reaction pathways, often leading to uncontrollable product distribution. We employ a single removable functional group to fulfill the dual role of attaining a reversible [2,3] and stabilizing radical int
Geminal difunctionalization of α-diazo arylmethylphosphonates: Synthesis of fluorinated phosphonates
Zhou, Yujing,Zhang, Yan,Wang, Jianbo
, p. 10444 - 10453 (2016/11/18)
A general approach towards diverse fluorinated phosphonates via geminal difunctionalization reactions of α-diazo arylmethylphosphonates is described. The diazo functionality (RR′CN2) is successfully converted to RR′CF2, RR′CHF, RR′CFBr or RR′CFNR′′2 groups by employing different fluorination reagents. A variety of fluorinated organophosphorus compounds were readily accessed in good to excellent yields from a common type of precursor.
Synthesis of Allenylphosphonates through Cu(I)-Catalyzed Coupling of Terminal Alkynes with Diazophosphonates
Wu, Chenggui,Ye, Fei,Wu, Guojiao,Xu, Shuai,Deng, Guisheng,Zhang, Yan,Wang, Jianbo
, p. 751 - 760 (2016/02/27)
Through the Cu(I)-catalyzed coupling of diazophosphonates with terminal alkynes, an efficient method for the synthesis of allenylphosphonates has been developed. Simple and inexpensive CuI is used as the catalyst and the reaction is conducted under mild conditions.
Cu(I)-Catalyzed Tandem Reaction of Carbene Coupling and Horner-Wadsworth-Emmons Type Olefination: Access toward Enynes
Zhou, Yujing,Ye, Fei,Zhou, Qi,Zhang, Yan,Wang, Jianbo
supporting information, p. 2024 - 2027 (2016/06/01)
A novel strategy to synthesize 1,3-enynes has been successfully developed based on Cu(I)-catalyzed cross-coupling of α-diazo phosphonates and alkynes with a subsequent Horner-Wadsworth-Emmons (HWE) type reaction. This method provides straightforward access to conjugated enynes with high efficiency, good stereoselectivity and excellent functional group compatibility. Copper(I) carbene migratory insertion plays a crucial role in this transformation.
Synthesis of Alkenylphosphonates through Palladium-Catalyzed Coupling of α-Diazo Phosphonates with Benzyl or Allyl Halides
Zhou, Yujing,Ye, Fei,Wang, Xi,Xu, Shuai,Zhang, Yan,Wang, Jianbo
, p. 6109 - 6118 (2015/06/30)
An efficient method for the synthesis of organophosphonates through palladium-catalyzed coupling of α-diazo phosphonates with benzyl or allyl halides has been developed. Trisubstituted alkenylphosphonates bearing versatile functional groups can be easily accessed in good yields and with excellent stereoselectivity through this method. Moreover, with similar strategy α-substituted vinylphosphonates can also be attained by the palladium-catalyzed coupling reaction of N-tosylhydrazones and aryl bromides. Migratory insertion of palladium carbene is proposed as the key step in this reaction.
Synthesis of Aryldiazoacetates through Palladium(0)-Catalyzed Deacylative Cross-Coupling of Aryl Iodides with Acyldiazoacetates
Ye, Fei,Wang, Chengpeng,Zhang, Yan,Wang, Jianbo
supporting information, p. 11625 - 11628 (2016/02/19)
Palladium(0)-catalyzed deacylative cross-coupling of aryl iodides and acyldiazocarbonyl compounds can be achieved at room temperature under mild reaction conditions. The coupling reaction represents a highly efficient and general method for the synthesis of aryldiazocarbonyl compounds, which have found wide and increasing applications as precursors for generating donor/acceptor-substituted metallocarbenes.
SALTS OF α-DIAZO "PHOSPHORUS ACIDS" - STARTING COMPOUNDS FOR PHOSPHONATE AND PHOSPHATE TRANSFER REAGENTS
Regitz, Manfred,Martin, Roland
, p. 163 - 166 (2007/10/02)
Pyrazoles bearing N-phosphonate and phosphate groups are well accessible from salts of α-diazo "phosphrus acids" and electron poor acetylenes.They are good phosphorylating reagents for protic nucleophiles.
