57386-83-1Relevant academic research and scientific papers
Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand
Liu, Feng,Wu, Na,Cheng, Xu
supporting information, p. 3015 - 3020 (2021/05/05)
Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.
A practical lewis base catalyzed electrophilic chlorination of arenes and heterocycles
Maddox, Sean M.,Nalbandian, Christopher J.,Smith, Davis E.,Gustafson, Jeffrey L.
supporting information, p. 1042 - 1045 (2015/03/30)
A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.
Metal and H2O2 free aerobic oxidative aromatic halogenation with [RNH3+] [NO3-]/HX and [BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl) as multifunctional ionic liquids
Prebil, Rok,Laali, Kenneth K.,Stavber, Stojan
supporting information, p. 2108 - 2111 (2013/06/05)
Novel multifunctional ionic liquids (ILs) are generated by addition of HBr or HCl to alkylammonium nitrates ([RNH3+] [NO 3-]) and to 3-methyl-1-(butyl-4-sulfonyl)imidazolium nitrate ([BMIM(SO3H)][NO3]). The resulting [RNH 3+] [NO3-]/HX and mono (3-methyl-1-(butyl-4-sulfonyl)imidazolium) monohalogenide mononitrate ([BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl)) systems act as solvent and promoter for aerobic oxidative halogenation of arenes under mild conditions in high yields that can be repeated over several cycles.
Aromatic substitution in ball mills: Formation of aryl chlorides and bromides using potassium peroxomonosulfate and NaX
Schmidt, Robert,Stolle, Achim,Ondruschka, Bernd
, p. 1673 - 1679 (2013/02/22)
Aryl chlorides and bromides are formed from arenes in a ball mill using KHSO5 and NaX (X = Cl, Br) as oxidant and halogen source, respectively. Investigation of the reaction parameters identified operating frequency, milling time, and the number of milling balls as the main influencing variables, as these determine the amount of energy provided to the reaction system. Assessment of liquid-assisted grinding conditions revealed, that the addition of solvents has no advantageous effect in this special case. Preferably activated arenes are halogenated, whereby bromination afforded higher product yields than chlorination. Most often reactions are regio- and chemoselective, since p-substitution was preferred and concurring side-chain oxidation of alkylated arenes by KHSO5 was not observed. The Royal Society of Chemistry.
Chlorination of aromatics with trichloroisocyanuric acid (TCICA) in bronsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf]: An economical, green protocol for the synthesis of chloroarenes
Hubbard, Abigail,Okazaki, Takao,Laali, Kenneth K.
, p. 923 - 927 (2008/03/17)
A survey study on electrophilic chlorination of aromatics with trichloroisocyanuric acid (TCICA) in Bronsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf] is reported. The reactions are performed under very mild conditions (at ～50°C) and give good to excellent yields, depending on the substrates. Chemoselectivity for mono- v. dichlorination can be tuned by changing the arene-to-TCICA ratio and the reaction time. The survey study and competitive experiments suggest that triprotonated/protosolvated TCICA is a selective/moderately reactive transfer-chlorination electrophile. Density functional theory was used as guide to obtain further insight into the nature of the chlorination electrophile and the transfer-chlorination step. CSIRO 2007.
Chlorination of aromatic compounds with chlorous acid under non-aqueous conditions
Muathen, Hussni A.
, p. 1493 - 1497 (2007/10/03)
The non-aqueous solution of chlorous acid is a versatile chlorinating agent for aromatic compounds, e.g. alkylbenzenes, anisoles, and acetanililides. It is also an effective chlorine-substitute for the conversion of aryl bromides into aryl chlorides under mild conditions. The stoichiometry of the chlorination reaction is ArH+3HOClO→ArCl+2ClO2+2H2O, and the mode of dissociation of chlorous acid in dichloromethanc is 3HOClO→HOCl+2ClO2+H2O.
Mild chlorination of aromatic compounds with tin(IV) chloride and lead tetraacetate
Muathen, Hussni A.
, p. 8863 - 8866 (2007/10/03)
SnCl4/Pb(OAc)4 acts as a safe source of Cl2 for the chlorination of aromatic compounds. A variety of aromatic compounds are effectively chlorinated with SnCl4/Pb(OAc)4 under mild conditions. The mixture is a selective chlorinating agent, particularly with polyalkylbenzenes, polycyclic aromatic compounds and anisoles.
Halogenation Using Quaternary Ammonium Polyhalides. XIX. Aromatic Chlorination of Arenes with Benzyltrimethylammonium Tetrachloroiodate
Kajigaeshi, Shoji,Ueda, Yasuhiro,Fujisaki, Shizuo,Kakinami, Takaaki
, p. 2096 - 2098 (2007/10/02)
The reaction of arenes with a calculated amount of benzyltrimethylammonium tetrachloroiodate in acetic acid at room temperature or at 70 deg C gave nuclear chloro-substituted arenes in fairly good yields.
