99180-09-3Relevant academic research and scientific papers
Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system
Satkar, Yuvraj,Ramadoss, Velayudham,Nahide, Pradip D.,García-Medina, Ernesto,Juárez-Ornelas, Kevin A.,Alonso-Castro, Angel J.,Chávez-Rivera, Ruben,Jiménez-Halla, J. Oscar C.,Solorio-Alvarado, César R.
, p. 17806 - 17812 (2018)
A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.
A Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO2, and Chloroalkanes
Jiang, Huanfeng,Zhang, Yu,Xiong, Wenfang,Cen, Jinghe,Wang, Lu,Cheng, Ruixiang,Qi, Chaorong,Wu, Wanqing
supporting information, p. 345 - 349 (2019/01/24)
A transition-metal-free three-phase four-component coupling reaction (3P-4CR) involving KCl, arynes, chloroalkanes and CO2 has been reported for the first time, enabling the incorporation of both chloro and CO2 into an aryne simultaneously. The reactions for the synthesis of different types of o-chloro benzoates can be selectively modulated by the chloroalkane utilized. The corresponding products can be alternatively transformed for postsynthetic functionalizations conveniently.
Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates
Mesgar, Milad,Daugulis, Olafs
supporting information, p. 4247 - 4250 (2017/08/23)
A general method for synthesis of 1,2-bis-trifluoromethylthioarenes has been developed. Arynes generated from silyl aryl triflates or halides react with bis(trifluoromethyl)disulfide to afford 1,2-bis-trifluoromethylthioarenes. Aryl, alkyl, ester, halide,
ELECTROCHROMIC COMPOSITION AND ELECTROCHROMIC ELEMENT
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Paragraph 0161; 0162, (2017/07/05)
An electrochromic composition has an anodic electrochromic compound and a cathodic electrochromic compound, in which the anodic electrochromic compound is represented by General Formula [1] and the cathodic electrochromic compound is represented by Genera
Total synthesis of a natural antioxidant and structure-activity relationships of related compounds
Jinno, Shuji,Otsuka, Naomi,Okita, Takaaki,Inouye, Kuniyo
, p. 1276 - 1283 (2007/10/03)
A total synthesis of benzodioxole derivative 1 was achieved via a palladium(0)-catalyzed cross-coupling reaction in a 68% overall yield (4 steps). A novel series of benzodioxoles bearing a variety of aromatic and heterocyclic rings was also prepared and the antioxidative activity evaluated using in vitro model systems. Structure-activity studies revealed that i) intramolecular hydrogen-bonding in the phenol moiety reduced activity, ii) introduction of disubstituents at the ortho location relative to the phenol increased activity, and iii) the methylenedioxy function contributed to stabilization of the phenoxy radical. Among of these compounds, 5,7-di-(4- methoxyphenyl)-4-methoxy-6-hydroxy-1,3-benzodioxole (7p) was the most favorable agent and more potent than n-propyl gallate.
