7385-85-5Relevant academic research and scientific papers
A comparative study of thallium(iii) and iodine(iii)-mediated ring contraction reactions for the synthesis of indane
Khan, Ajmir,Silva, Luiz F.,Rabnawaz, Muhammad
supporting information, p. 2078 - 2084 (2021/02/06)
Reported herein is a comparative study of the synthesis of indaneviaring contraction reaction, mediated by iodine(iii) and thallium(iii). A series of protected 1,2-dihydronaphthalenes were synthesized and subjected to hydroxy(tosyloxy)iodobenzene (HTIB) and thallium(iii) nitrate trihydrate (TTN) in trimethyl orthoformate (TMOF) to compare the percent yields provided by both oxidizing agents. The yields of the ring contracted products (indanes) were in the range of 61-88% for reactions performed with TTN·3H2O in TMOF. However, the yields were found to be significantly lower (e.g., 18-34%) when using HTIB in TMOF with some addition products. This study provides an important development related to the efficacy of the two oxidizing agents for ring contraction reaction.
Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols
Ma, Jinfeng,Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, (2021/10/26)
A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.
Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C-O and C-H Cleavage
Zhang, Liangwei,Liu, Long,Huang, Tianzeng,Dong, Qizhi,Chen, Tieqiao,Chen, Tieqiao
, p. 2189 - 2196 (2020/06/05)
A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C-O and C-H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition t
Phenol Derivatives in Ruthenium-Catalyzed C–H Arylation: A General Synthetic Access to Azole-Based Congested Polyaromatics
Roger, Julien,Hierso, Jean-Cyrille
supporting information, p. 4953 - 4958 (2018/09/25)
Aryl triflates and related phenolates are suitable electrophile coupling partners for the ruthenium-catalyzed direct arylation of heteroaromatic substrates using azole N-directed Csp2–H activation. We report herein convenient conditions for the efficient ortho-C–H functionalization of aryl-pyrazoles, thiazoles and pyridines in which [RuCl2(p-Cym)]2 precatalyst is employed with pivalic acid (PivOH) as co-catalyst. Different phenolate derivatives were successfully coupled, which tolerate a large scope of electron-rich substituents in para-, meta- and highly hindered ortho-position. Electron-withdrawing aryl triflates were found to be less reactive, making the general reactivity of these electrophiles complementary to those of aryl chlorides and deactivated bromides. This cost-effective ruthenium C–H activation/arylation synthesis of poly(hetero)aromatics was concurrently examined using triflates, mesylates, sulfonates, and carbonates, and was also successfully extended to the use of diethyl carbonate as an eco-friendly solvent.
Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate
Wang, Jiawang,Zhao, Jianhong,Gong, Hegui
supporting information, p. 10180 - 10183 (2017/09/23)
This work describes the cross-electrophile methylation of aryl bromides and aryl tosylates with methyl tosylate. The mild reaction conditions allow effective methylation of a wide set of heteroaryl electrophiles and dimethylation of dibromoarenes.
Formation of Phenalenone Skeleton by an Unusual Rearrangement Reaction
Sasaki, Sayaka,Azuma, Eriko,Sasamori, Takahiro,Tokitoh, Norihiro,Kuramochi, Kouji,Tsubaki, Kazunori
supporting information, p. 4846 - 4849 (2017/09/23)
The frame rearrangement reaction of dinaphthyl ketones, possessing hydroxy groups at appropriate positions, into phenalenone derivatives under acidic conditions was discovered serendipitously. Although this rearrangement had limited scope, its mechanism was unusual, involving the division of naphthalene rings into one phenalenone ring and one benzene ring. The reaction mechanism was elucidated by direct determination of intermediate structures using 1H NMR measurements. The generated phenalenones are expected to be key intermediates toward natural products and functional materials.
Oxidative Addition of Aryl Electrophiles to a Prototypical Nickel(0) Complex: Mechanism and Structure/Reactivity Relationships
Bajo, Sonia,Laidlaw, Gillian,Kennedy, Alan R.,Sproules, Stephen,Nelson, David J.
supporting information, p. 1662 - 1672 (2017/04/28)
Detailed kinetic studies of the reaction of a model Ni0 complex with a range of aryl electrophiles have been conducted. The reactions proceed via a fast ligand exchange pre-equilibrium, followed by oxidative addition to produce either [NiIX(dppf)] (and biaryl) or [NiII(Ar)X(dppf)]; the ortho substituent of the aryl halide determines selectivity between these possibilities. A reactivity scale is presented in which a range of substrates is quantitatively ranked in order of the rate at which they undergo oxidative addition. The rate of oxidative addition is loosely correlated to conversion in prototypical cross-coupling reactions. Substrates that lead to NiI products in kinetic experiments produce more homocoupling products under catalytic conditions.
Palladium Catalyzed Arylation and Benzylation of Nitroarenes Using Aryl Sulfonates and Benzyl Acetates
Yi, Zubaoyi,Aschenaki, Yodit,Daley, Ryan,Davick, Stephen,Schnaith, Abigail,Wander, Rylee,Kalyani, Dipannita
, p. 6946 - 6957 (2017/07/13)
Pd-catalyzed arylation or benzylation of nitroazoles using aryl sulfonates or benzyl acetates is described. Electronically varied aryl tosylates and mesylates, as well as benzyl acetates, afford the arylated and benzylated products. Arylation of nitrobenz
Phosphorylation of Alkenyl and Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis
Liao, Li-Li,Gui, Yong-Yuan,Zhang, Xiao-Bo,Shen, Guo,Liu, Hui-Dong,Zhou, Wen-Jun,Li, Jing,Yu, Da-Gang
supporting information, p. 3735 - 3738 (2017/07/26)
A phosphorylation of alkenyl and aryl C-O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are g
Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
Rostami, Abed,Rostami, Amin,Ghaderi, Arash,Gholinejad, Mohammad,Gheisarzadeh, Sajedeh
, p. 5025 - 5038 (2017/10/06)
Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
