3972-56-3Relevant academic research and scientific papers
Photochemical Sandmeyer-type Halogenation of Arenediazonium Salts
Belitz, Florian,Goo?en, Lukas J.,Manu Martínez, ángel,Schmid, Rochus,Sivendran, Nardana,Sowa Prendes, Daniel
supporting information, (2022/01/19)
Trihalide salts were found to efficiently promote photochemical dediazotizing halogenations of diazonium salts. In contrast to classical Sandmeyer reactions, no metal catalysts are required to achieve high yields and outstanding selectivities for halogena
Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions
Patra, Tuhin,Mukherjee, Satobhisha,Ma, Jiajia,Strieth-Kalthoff, Felix,Glorius, Frank
, p. 10514 - 10520 (2019/07/12)
Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.
Ligand-free nickel-catalyzed Kumada couplings of aryl bromides with tert-butyl Grignard reagents
Wu, Zhenghan,Si, Tengda,Xu, Guangqing,Xu, Bin,Tang, Wenjun
supporting information, p. 597 - 600 (2019/01/05)
A ligand-free nickel-catalyzed Kumada cross-coupling of aryl bromides and tert-butyl Grignard reagents led to the formation of a series of tert-butyl aryls in moderate to good yields, excellent tBu/iBu ratios, and good functional group compatibility. A radical coupling process is indicated and a mechanism with a Ni(I)-Ni(III) catalytic cycle is proposed.
Benzo polyaza and phosphole oxygen ligand and complex containing same, preparation method and application
-
Paragraph 0152; 0153; 0154; 0155; 0156, (2019/01/16)
The invention discloses a benzo polyaza and phosphole oxygen ligand and a complex containing same, a preparation method and application. The invention provides a benzo polyaza and phosphole oxygen ligand as shown in formula I and a complex containing same. A complex of the benzo polyaza and phosphole oxygen ligand and a transition metal halide enables direct coupling of carbon-carbon bonds betweenbig steric hindrance alkyl and aryl; the reaction conditions are gentle; the catalyzing efficiency is high; the coupling reaction process of the carbon-carbon bonds between big steric hindrance alkyland aryl can be extremely simplified; the practicability is high; the reaction cost can be obviously decreased, and the reaction period is reduced; the complex is free from other side products without being required in the catalyzing process. The formula refers to the description.
Iron(III)-mediated photocatalytic selective substitution of aryl bromine by chlorine with high chloride utilization efficiency
Wang, Ying,Li, Lina,Ji, Hongwei,Ma, Wanhong,Chen, Chuncheng,Zhao, Jincai
supporting information, p. 2344 - 2346 (2014/03/21)
An iron(III)-mediated photocatalytic method for the conversion of aryl, heteroaryl and polycyclic aromatic bromides to the corresponding chlorides with high selectivity has been achieved successfully. The mild reaction conditions and high chloride utilization efficiency promise a bright future for chlorination reactions. The Royal Society of Chemistry 2014.
Halogen exchange via a halogenation of diaryliodonium salts with cuprous halide
Li, Jian,Liu, Li,Ding, Dong,Sun, Jiang-Tao
, p. 541 - 548 (2014/01/06)
An efficient halogenation reaction has been developed with diaryliodonium salts and cuprous halides. Various diaryliodonium salts 1 could perform the reaction with readily available CuBr or CuCl in CH3CN at 80°C, assembling bromoarenes or chloroarenes in up to 92% yields. This provides us a method for the transformation from iodoarenes to other haloarenes.
Microwave-assisted silica-supported aluminum chloride-catalyzed Friedel-Crafts alkylation
Zupp, Laurine R.,Campanella, Veronica L.,Rudzinski, Diandra M.,Beland, Franois,Priefer, Ronny
, p. 5343 - 5346 (2012/10/30)
Microwave irradiation is a popular method in organic synthesis to achieve high yields in shorter reaction times. This decreases total 'man-hours' in a synthetic setting. Another technique used in organic chemistry to decrease manual manipulations, is solid support reagents. The benefits of this approach is that upon completion of a reaction, a simple filtration can be performed which expedites the work-up and also produces less organic waste. Friedel-Crafts alkylation has been explored using microwave chemistry as well as with solid-supported reagents. In comparison with traditional heating, as well as with AlCl3, superior yields were observed with silica-gel bound aluminum chloride (Si-AlClx) when microwave irradiated for only 5 min.
Hypochlorite-induced ipso-substitution reactions of aromatic alcohols and related compounds
Carrillo, Hector V.,Rodriguez, Angelica Y.,Landolt, Robert G.,Hendrickson, William H.
experimental part, p. 2069 - 2071 (2011/10/09)
Organic solvent extracts derived from aqueous hypochlorite/phase-transfer catalyst solutions induce rapid and efficient ipso substitution of aromatic carbinols and related substrates. The key parameter impacting rates and yields is pH of the original hypochlorite/phase-transfer catalyst component. Georg Thieme Verlag Stuttgart - New York.
Ultrasound assisted Friedel-Crafts acylation of aromatics using ferric sulphate as catalyst
Sridharan, Anandhi,Gopalakrishnan, Geetha
experimental part, p. 1192 - 1195 (2011/10/18)
The use of ultrasound in the acylation reactions of various aromatics and polyaromatics with different acyl chlorides, in the presence of catalytic amount of ferric sulphate at room temperature, gives good yields of the respective ketones with a short reaction time. A facile and simple synthesis of various aromatic ketones using Friedel-Crafts acylation has been established from the corresponding acid chlorides and aromatic or polyaromatic compounds, respectively under mild reaction conditions with shorter reaction times (30-45 min) and in reasonable yields. This method offers the advantage of low cost and ease of purification of the products because of the small amount of ferric sulphate used in these reactions.
Metal-free chlorodeboronation of organotrifluoroborates
Molander, Gary A.,Cavalcanti, Livia N.
experimental part, p. 7195 - 7203 (2011/10/13)
A mild and metal-free method for the chlorodeboronation of organotrifluoroborates using trichloroisocyanuric acid (TCICA) was developed. Aryl-, heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates were converted into the corresponding chlorinated products in good yields. This method proved to be tolerant of a broad range of functional groups.
