116248-64-7Relevant academic research and scientific papers
Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
Zhao, Bin,Hammond, Gerald B.,Xu, Bo
, (2021/09/13)
We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed C-H Olefination of Arenes with Molecular Oxygen as the Sole Oxidant
Yadav, Mamta,Jat, Ram Singh,Sarma, Bibek,Bhanuchandra
, p. 2269 - 2276 (2021/03/03)
Pd(II)-catalyzed C-H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulf
Palladium-catalyzed regioselective arylation of arene C-H bond assisted by the removable 2-pyridylsulfinyl group
Zhang, Xunbin,Yu, Ming,Yao, Jinzhong,Zhang, Yuhong
supporting information; experimental part, p. 463 - 467 (2012/03/11)
A palladium-catalyzed arylation of arene C-H bond assisted by a removable 2-pyridylsulfinyl group is described. The reaction employs aryltrifluoroborates as the arylation reagent, leading to the corresponding products in moderate to good yield with broad substrate scope. The directing group can be removed or converted to other useful functionalities, which showcases the potential synthetic application of the methodology. Georg Thieme Verlag Stuttgart · New York.
Modifiable sulfur tethers as directing groups for aromatic C-H acetoxylation reactions
Richter, Heinrich,Beckendorf, Stephan,Mancheno, Olga Garcia
supporting information; experimental part, p. 295 - 302 (2011/04/16)
A designed new class of modifiable sulfur tethers for aromatic C-H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.
2-pyridyl sulfoxide: A versatile and removable directing group for the PdII-catalyzed direct C-H olefination of arenes
Garcia-Rubia, Alfonso,Fernandez-Ibanez, M. Ungeles,Gomez Arrayas, Ramon,Carretero, Juan Carlos
supporting information; experimental part, p. 3567 - 3570 (2011/05/12)
Removable and versatile: The 2-pyridylsulfinyl group has proved to be an efficient directing group in the PdII-catalyzed aryl ortho C-H olefination. This catalyst system enables the sequential double olefination to give asymmetrically di-ortho-functionalized arenes. The sulfinyl directing group can be easily cleaved, providing access to 1,3-disubstituted arenes, or transformed into a thiol group.
Palladium(II)-catalyzed direct alkenylation and arylation of arenes: Removable 2-pyridylsulfinyl group assisted C-H bond activation
Yu, Ming,Liang, Zunjun,Wang, Yongyong,Zhang, Yuhong
experimental part, p. 4987 - 4994 (2011/08/03)
Palladium-catalyzed C-H activation reactions directed by a removable 2-pyridylsulfinyl group were developed. Aromatic olefination products were formed in good yields on treatment of 2-(phenylsulfinyl)pyridines with alkenes in the presence of a Pd catalyst
Efficient palladium catalyzed synthesis of heteroaromatic sulfoxides
Colobert, Fran?oise,Ballesteros-Garrido, Rafael,Leroux, Frédéric R.,Ballesteros, Rafael,Abarca, Belén
, p. 6896 - 6899 (2008/02/12)
The present Letter describes the efficient synthesis of novel heteroaromatic sulfoxides by means of a palladium catalyzed heteroarylation of sulfenate anions. Triazolopyridine, pyridine and thiophene sulfoxides can be obtained under mild conditions and in high yield from the corresponding heteroaryl bromides.
