2206-48-6Relevant academic research and scientific papers
Visible-Light-Promoted Iron-Catalyzed C(sp2)–C(sp3) Kumada Cross-Coupling in Flow
Wei, Xiao-Jing,Abdiaj, Irini,Sambiagio, Carlo,Li, Chenfei,Zysman-Colman, Eli,Alcázar, Jesús,No?l, Timothy
, p. 13030 - 13034 (2019/07/18)
A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada–Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.
Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses
Solyntjes, Sven,Neumann, Beate,Stammler, Hans-Georg,Ignat'ev, Nikolai,Hoge, Berthold
, p. 1568 - 1575 (2017/02/10)
Commercially available BiPh3was treated with perfluoroalkylphosphinic acids [for example, (C2F5)2P(O)OH] to generate novel, highly Lewis acidic bismuth(III) perfluoroalkylphosphinates of the type PhxBi[RF2PO2]3?x(x=0, 1, 2) (RF=-C2F5, -C4F9). The first bismuth(V) perfluoroalkylphosphinate, Ph3Bi[(C2F5)2PO2]2, was synthesized from Ph3BiCl2and Ag[(C2F5)2PO2]. Examples for the successful application of the catalytically active bismuth(III) and bismuth(V) phosphinates in carbon–carbon bond forming reactions, such as Friedel–Crafts acylation and alkylation, Diels–Alder, Strecker and Mannich reaction, are presented.
Room Temperature Catalyst System for the Hydroarylation of Olefins
Lee, Siu Yin,Villani-Gale, Alexander,Eichman, Chad C.
supporting information, p. 5034 - 5037 (2016/10/14)
A simple protocol for the hydroarylation of olefins to yield diarylmethine products is described. A Friedel-Crafts-type synthetic strategy allows direct access to biorelevant products in high atom efficiency. A combination of substoichiometric amounts of TMSCl and ZnBr2 promotes a rapid hydroarylation process at ambient temperature. The method is high yielding and is amenable to scale-up protocols.
Sterically congested phosphonium borate acids as effective Br?nsted acid catalysts
Sinha, Arup,Jaiswal, Amit K.,Young, Rowan D.
, p. 36 - 43 (2016/12/06)
Phosphonium borate acids [HPPh2(C6F5)][B(C6F5)4] (2), [HPMes2(C6F5)][B(C6F5)4] (3) and [HPMes(C6F5)2][B(C6F5)4] (4) were synthesized via heterolytic dihydrogen cleavage in the presence of triisopropylsilylium and characterized by spectroscopic and crystallographic methods. Br?nsted acid catalysis using compounds 2–4 proved to be efficient for a number of challenging reactions (namely ionic hydrogenation, hydroamination and hydroarylation), owing to the restrained nucleophilicity of the sterically hindered conjugate bases. Reactivity of compounds 2–4 suggests that their pKavalues are similar to that of diethyl oxonium acid.
Nickel-catalyzed selective oxidative radical cross-coupling: An effective strategy for inert Csp3-H functionalization
Liu, Dong,Li, Yuxiu,Liu, Chao,Lei, Aiwen,Qi, Xiaotian,Lan, Yu.
supporting information, p. 998 - 1001 (2015/03/30)
An effective strategy for inert Csp3-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated. Density functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments. Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp3-H arylation products in good yields.
Synthesis of iron(III) complex bearing tridentate β-Aminoketonato Ligand: Application to iron-catalyzed cross-coupling reaction of arylmagnesium bromides with alkyl halides
Yamaguchi, Yoshitaka,Ando, Hiroaki,Nagaya, Makoto,Hinago, Hideto,Ito, Takashi,Asami, Masatoshi
supporting information; experimental part, p. 983 - 985 (2011/12/05)
A tridentate β-aminoketonato iron complex was prepared by the reaction of lithium β-aminoketonato with FeCl3. This iron complex was found to be an efficient catalyst for the crosscoupling reaction between arylmagnesium bromides and alkyl halides.
Ruthenium-catalyzed para-selective oxidative cross-coupling of arenes and cycloalkanes
Guo, Xiangyu,Li, Chao-Jun
supporting information; experimental part, p. 4977 - 4979 (2011/11/12)
A novel, direct para-selective oxidative cross-coupling of benzene derivatives with cycloalkanes catalyzed by ruthenium was developed. A wide range of arenes bearing electron-withdrawing substituents was functionalized directly with simple cycloalkanes with high para-selectivity; arenes with electron-donating groups were mainly para-functionalized. Benzoic acid can be used directly.
Chlorine borrowing: An efficient method for an easier use of alcohols as alkylation agents
Makowski, Philippe,Rothe, Regina,Thomas, Arne,Niederberger, Markus,Goettmann, Frederic
scheme or table, p. 34 - 37 (2010/04/22)
Chlorine functionalised tin dioxide nanoparticles proved able to partially convert alcohols into the corresponding chlorides, which act as alkylation agents with an increased electrophilicity, as evidenced on ether formation and Friedel-Crafts reactions.
Highly efficient gold(III)-catalyzed intermolecular hydroarylation of unactivated alkenes with arenes under mild conditions
Xiao, Ya-Ping,Liu, Xin-Yuan,Che, Chi-Ming
experimental part, p. 494 - 501 (2009/06/06)
A simple and efficient method for functionalization of electron-rich arenes and heteroarenes with unactivated alkenes by Au(III)-catalyzed intermolecular hydroarylation under mild reaction conditions was developed. This method features a short reaction time (5 h) under mild conditions and has a broad substrate scope, including electron-rich arenes and heteroarenes, terminal and internal substituted aryl alkenes, and unactivated aliphatic alkenes.
