3899-92-1Relevant articles and documents
Synthesis, anti-oomycete activity, and SAR studies of paeonol derivatives
Tian, Yue-E,Sun, Di,Han, Xiao-Xiao,Yang, Jin-Ming,Zhang, Song,Feng, Nan-Nan,Zhu, Li-Na,Xu, Zhong-Yuan,Che, Zhi-Ping,Liu, Sheng-Ming,Lin, Xiao-Min,Jiang, Jia,Chen, Gen-Qiang
, p. 138 - 149 (2020/02/11)
Three series of sulfonate derivatives of paeonol were synthesized and screened in?vitro for their anti-oomycete activity against P. capsici, respectively. Among all the compounds, 4m displayed the best promising and pronounced anti-oomycete activity again
Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information, p. 19257 - 19262 (2019/12/02)
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
Coupling of C(sp3)-H bonds with C(sp2)-O electrophiles: mild, general and selective
Gui, Yong-Yuan,Liao, Li-Li,Sun, Liang,Zhang, Zhen,Ye, Jian-Heng,Shen, Guo,Lu, Zhi-Peng,Zhou, Wen-Jun,Yu, Da-Gang
supporting information, p. 1192 - 1195 (2017/02/05)
Herein is reported the mild and general coupling of amine/ether C(sp3)-H bonds with various kinds of C(sp2)-O electrophiles with high selectivity and efficiency. Valuable allylic/benzylic amines are generated in moderate to excellent yields. The utility of this transformation is demonstrated by a broad substrate scope (>50 examples), good functional group tolerance and facile product modification.
Aryl tosylates as non-ionic photoacid generators (PAGs): Photochemistry and applications in cationic photopolymerizations
Torti, Edoardo,Della Giustina, Gioia,Protti, Stefano,Merli, Daniele,Brusatin, Giovanna,Fagnoni, Maurizio
, p. 33239 - 33248 (2015/04/27)
The irradiation of various substituted aryl tosylates was investigated in a solution and homolysis of the ArO-SO2C6H4CH3 bond was the path exclusively observed. The corresponding phenols and photo-Fries adducts were obtained and p-toluenesulfinic and p-toluenesulfonic acids were liberated. The nature and amount of the acid photoreleased were tuned by changing the reaction conditions and the nature and position of the aromatic substituents. In deaerated solutions p-toluenesulfinic acid was formed exclusively, whereas under oxygenated conditions the stronger p-toluenesulfonic acid was released, as shown by HPLC ion chromatography analyses. ArO-S bond photocleavage takes place from the singlet state, as confirmed by laser flash photolysis experiments, and competitive intersystem crossing can make the aryl tosylate unreactive when a nitro group is present. The application of these aryl tosylates as non-ionic photoacid generators (PAGs) in hybrid organic/inorganic sol-gel photoresists has been explored.
Nickel-catalyzed C-P coupling of aryl mesylates and tosylates with H(O)PR1R2
Shen, Chaoren,Yang, Guoqiang,Zhang, Wanbin
supporting information; body text, p. 3500 - 3505 (2012/05/20)
A method was developed for the nickel-catalyzed phosphonylation of aryl mesylates and tosylates with H(O)PR1R2. To the best of our knowledge, this is the first example of nickel-catalyzed C-P coupling of aryl mesylates and tosylates. Most of the substrates gave moderate to good yields under our catalytic system.
Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts
Goossen, Luksa J.,Rodriguez, Nuria,Lange, Paul P.,Linder, Christophe
supporting information; experimental part, p. 1111 - 1114 (2010/04/29)
(Figure Presented) A bimetallic copper/palladium catalyst system is disclosed that enables the use of tosylates as carbon electrophiles in decarboxylative coupling reactions. A variety of aromatic carboxylate salts, regardless of their substitution pattern, have been coupled with these inexpensive and readily available electrophiles to give the corresponding biaryl compounds in good yields (see scheme).
Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature
Ogata, Tokutaro,Hartwig, John F.
supporting information; experimental part, p. 13848 - 13849 (2009/02/07)
Mild palladium-catalyzed aminations of aryl tosylates and the first aminations of heteroaryl tosylates are described. In the presence of the combination of L2Pd(0) (L = P(o-tol)3) and the hindered Josiphos ligand CyPF-t-Bu, a variety of primary alkylamines and arylamines react with both aryl and heteroaryl tosylates at room temperature to form the corresponding secondary arylamines in high yields with complete selectivity for the monoarylamine. These reactions at room temperature occur in many cases with catalyst loadings of 0.1 mol % and 0.01 mol % in one case, constituting the most efficient aminations of aryl tosylates by nearly 2 orders of magnitude. This catalyst is made practical by the development of a convenient method to synthesize the L2Pd(0) precursor. This complex is stable to air as a solid. In contrast to conventional relative rates for reactions of aryl sulfonates, the reactions of aryl tosylates are faster than parallel reactions of aryl triflates, and the reactions of aryl tosylates are faster than parallel or competitive reactions of aryl chlorides. Copyright
New preparative method of aryl tosylates by using organobismuth reagents
Sakurai, Naoto,Mukaiyama, Teruaki
, p. 928 - 929 (2008/02/12)
A new method for the preparation of aryl tosylates by using pentavalent bismuth is described. Treatment of 10-arylphenothiabismine 5,5-dioxides, m-chloroperoxybenzoic acid (MCPBA) and p-toluenesulfonic acid monohydrate in dichloromethane affords aryl tosy
A new preparative method of aryl sulfonate esters by using cyclic organobismuth reagents
Sakurai, Naoto,Mukaiyama, Teruaki
, p. 771 - 790 (2008/09/18)
A new method for the preparation of aryl sulfonate esters by using a cyclic pentavalent bismuth is described. Aryl sulfonate esters are formed in good to high yields by treating 10-arylphenothiabismine 5,5-dioxides, m-chloroperoxybenzoicacid (m-CPBA)and various sulfonic acids in dichloromethane.
