739-61-7Relevant academic research and scientific papers
Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions
Zhu, Xiancui,Xu, Mengchen,Sun, Jinrong,Guo, Dianjun,Zhang, Yiwei,Zhou, Shuangliu,Wang, Shaowu
, p. 5213 - 5218 (2021/10/19)
Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.
Convenient synthesis of phosphinecarboxamide and phosphinecarbothioamide by hydrophosphination of isocyanates and isothiocyanates
Itazaki, Masumi,Matsutani, Takanari,Nochida, Tomoya,Moriuchi, Toshiyuki,Nakazawa, Hiroshi
supporting information, p. 443 - 445 (2020/01/13)
Reactions of isocyanates with primary and secondary phosphines without solvent at room temperature afforded the corresponding phosphinecarboxamide (RN(H)COPR′2) in excellent yields. This reaction system is applicable for isothiocyanates. The co
The phosphinoboration of carbodiimides, isocyanates, isothiocyanates and CO2
Geier, Stephen J.,Lafortune, James H. W.,Zhu, Diya,Kosnik, Stephanie C.,Macdonald, Charles L.B.,Stephan, Douglas W.,Westcott, Stephen A.
supporting information, p. 10876 - 10885 (2017/08/30)
The transition metal-free addition of phosphinoboronate ester Ph2PBpin (pin = 1,2-O2C2Me4) to heterocumulenes including carbodiimides, isocyanates, isothiocyanates and carbon dioxide has been investigated. The corresponding 1,2-addition products were readily prepared at room temperature without the need of a catalyst or added base. Addition of methanol to the compounds derived from addition of Ph2PBpin to carbodiimides, isocyanates, and isothiocyanates resulted in traditional hydrophosphination products. The methodology developed in this study provides a simple and elegant route for the generation of a wide range of functionalized phosphines. The phosphinoboronate ester Ph2PBpin also selectively and reversibly adds to CO2 at room temperature in a 1,2-manner.
Addition of E-H (E = N, P, C, O, S) Bonds to Heterocumulenes Catalyzed by Benzimidazolin-2-iminato Actinide Complexes
Liu, Heng,Fridman, Natalia,Tamm, Matthias,Eisen, Moris S.
supporting information, p. 3896 - 3903 (2017/10/30)
The synthesis and characterization of benzimidazolin-2-iminato actinide(IV) complexes [(BimR1/R2N)An(N{SiMe3}2)3] (An = U, Th) (1-6) is reported. All complexes were obtained in high yields, and their solid state structures were established through single-crystal X-ray diffraction analysis. Using 1-6 as precatalysts, the addition of mono- and bifunctional E-H (E = N, P, C, O, S) substrates to various heterocumulenes, including carbodiimides, isocyanates, and isothiocyanates, was investigated, affording the respective addition products in high yields under very mild reaction conditions. Various amines were applicable to this reaction, indicating a large scope capability of amine nucleophiles for the insertion process.
Catalytic insertion of E-H bonds (E = C, N, P, S) into heterocumulenes by amido-actinide complexes
Batrice, Rami J.,Eisen, Moris S.
, p. 939 - 944 (2016/02/05)
We report herein the actinide-mediated insertion of E-H bonds (E = C, N, P, S) into various heterocumulenes including carbodiimides, isocyanates, and isothiocyanates. The precatalysts are prepared by a simple, one-pot procedure using readily available sta
Synthesis of Bis(NHC)-Based CNC-Pincer Rare-Earth-Metal Amido Complexes and Their Application for the Hydrophosphination of Heterocumulenes
Gu, Xiaoxia,Zhang, Lijun,Zhu, Xiancui,Wang, Shaowu,Zhou, Shuangliu,Wei, Yun,Zhang, Guangchao,Mu, Xiaolong,Huang, Zeming,Hong, Dongjing,Zhang, Feng
, p. 4553 - 4559 (2015/10/06)
The bis(NHC) (NHC = N-heterocyclic carbene)-based CNC-pincer rare-earth-metal amido complexes LRE[N(SiMe3)2]2 (L = 4-CH3-2-{R-[N(CH)2CN]}C6H3]2N; L2, R = CH
Actinide-Mediated Catalytic Addition of E-H Bonds (E=N, P, S) to Carbodiimides, Isocyanates, and Isothiocyanates
Karmel, Isabell S.R.,Tamm, Matthias,Eisen, Moris S.
supporting information, p. 12422 - 12425 (2015/10/12)
Unprecedented catalytic reactivity of actinide coordination complexes toward heterocumulenes, such as carbodiimides, isocyanates, and isothiocyanates is reported. The mono(imidazolin-2-iminato) thorium(IV) complex [Th(ImDippN){N(SiMe3)2}3] (1) was applied as a precatalyst for the addition of E-H (E=N, P, S) bonds to the Y≡C≡X core (Y=R2N; X=NR2, O, S) of carbodiimides, isocyanates, and isothiocyanates. The respective insertion products were obtained in high yields under mild reaction conditions, with complex 1 displaying high tolerance toward functional groups and heteroatoms. New reactivity: The mono(imidazolin-2-iminato) thorium complex [Th(ImDippN){N(SiMe3)2}3] was successfully applied as an active catalyst for the addition of E-H (E=N, P, S) bonds across the central Y≡N≡C≡X linkage of carbodiimides, isocyanates and isothiocyanates, yielding the respective insertion products in high yields and under mild reaction conditions.
Insertion reactions and catalytic hydrophosphination of heterocumulenes using α-metalated N, N-dimethylbenzylamine rare-earth-metal complexes
Behrle, Andrew C.,Schmidt, Joseph A. R.
, p. 1141 - 1149 (2013/05/09)
The reactivity of homoleptic α-metalated dimethylbenzylamine lanthanide complexes (α-Ln(DMBA)3; Ln = La, Y; DMBA = α-deprotonated dimethylbenzylamine) was probed through a series of stoichiometric insertion and catalytic hydrophosphination reactions. Both rare-earth-metal species inserted 3 equiv of various carbodiimides to form the corresponding homoleptic amidinates. α-La(DMBA)3 was also found to be a useful precatalyst for the room-temperature hydrophosphination of heterocumulenes to form phosphaguanidines, phosphaureas, and phosphathioureas in moderate to excellent isolated yields. Furthermore, through a series of stepwise stoichiometric protonation and insertion reactions, a plausible mechanism for the hydrophosphination catalysis was investigated.
