85387-86-6Relevant academic research and scientific papers
One-pot synthesis of sulfones via Ni(II)-catalyzed sulfonylation of boronic acids, Na2S2O5 and benzylic ammonium salts
Zhu, Haibo,Liu, Yishuai,Zhang, Yingying,Yang, Liu,Meng, Jia,Li, Qian,Gong, Bozhen,Xie, Zongbo,Le, Zhang-Gao
, (2021/03/08)
A one-pot nickel-catalyzed synthesis of (hetero)aryl alkyl sulfones from readily available boronic acids, sodium metabisulfite and benzylic ammonium salts as electrophiles is described. This general and efficient synthetic process is of broad scope, occurs in two steps, and delivers structural diverse sulfones, and the intermediate sulfinate is isolated. The transformation exhibits application of benzylic ammonium salts as novel electrophiles for direct insertion of SO2 as a novel area to be investigated.
A general and practical sulfonylation of benzylic ammonium salts with sulfonyl hydrazides for the synthesis of sulfones
Zhu, Haibo,Zhang, Yingying,Liu, Yishuai,Yang, Liu,Xie, Zongbo,Jiang, Guofang,Le, Zhang-Gao
supporting information, (2020/05/06)
A practical and efficient approach adopting transition-metal-free cross-coupling of sulfonyl hydrazides with benzyl ammonium salts has been developed to synthesize benzyl sulfones using Cs2CO3 as base under mild conditions. The protocol employs stable and easy to handle coupling partners, and is endowed with good substrate compatibility, leading to functional benzyl sulfones in good yields.
Benzylic C(sp3)-H bond sulfonylation of 4-methylphenols with the insertion of sulfur dioxide under photocatalysis
Gong, Xinxing,Chen, Jiahao,Lai, Lifang,Cheng, Jiang,Sun, Jiangtao,Wu, Jie
supporting information, p. 11172 - 11175 (2018/10/20)
Sulfonylation of the benzylic C-H bond is developed through a three-component reaction of aryldiazonium tetrafluoroborates, 4-methylphenols and sodium metabisulfite (Na2S2O5). The inorganic sulfite of sodium metabisulfite is used as the SO2 surrogate. In this transformation, benzylic C(sp3)-H bond sulfonylation is achieved in the presence of a photocatalyst under visible light. A radical pathway involving the arylsulfonyl radical and intermolecular hydrogen atom abstraction is proposed.
Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone
Nambo, Masakazu,Crudden, Cathleen M.
supporting information, p. 742 - 746 (2014/01/23)
Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals. Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. Copyright
Palladium-catalyzed direct α-arylation of methyl sulfones with aryl bromides
Zheng, Bing,Jia, Tiezheng,Walsh, Patrick J.
supporting information, p. 1690 - 1693 (2013/06/26)
A direct and efficient approach for palladium-catalyzed arylation of aryl and alkyl methyl sulfones with aryl bromides has been developed. The catalytic system affords arylated sulfones in good to excellent yields (73-90%).
Palladium-catalyzed substitution and cross-coupling of benzylic fluorides
Blessley, George,Holden, Patrick,Walker, Matthew,Brown, John M.,Gouverneur, Veronique
, p. 2754 - 2757 (2012/07/16)
Benzylic fluorides are suitable substrates for Pd(0)-catalyzed Tsuji-Trost substitution using carbon, nitrogen, oxygen, and sulfur nucleophiles and for cross-coupling with phenylboronic acid. For the bifunctional substrate 4-chlorobenzyl fluoride, fine-tuning of the reaction conditions allows for the regioselective displacement of either the chlorine or fluorine substituent. The leaving group ability of fluoride vs other groups displaced in substitution is CF3CO2 ≈ p-NO2C6H 4CO2 ≈ OCO2CH3 > F > CH3CO2, a ranking similar to allylic fluorides under Pd catalysis.
Palladium-catalyzed Negishi α-arylation of alkylsulfones
Zhou, Gang,Ting, Pauline C.,Aslanian, Robert G.
experimental part, p. 939 - 941 (2010/05/18)
A general, mild catalytic system for α-monoarylation of various alkyl sulfones is described that utilizes palladium-catalyzed Negishi cross-coupling approach.
Transformation of carbonates into sulfones at the benzylic position via palladium-catalyzed benzylic substitution
Kuwano, Ryoichi,Kondo, Yutaka,Shirahama, Tsuyoshi
, p. 2973 - 2975 (2007/10/03)
(Chemical Equation Presented) The nucleophilic substitution of benzylic carbonates with sodium arenesulfinates was catalyzed by the palladium complex generated in situ from [Pd(η3-C3H5)Cl] 2 and DPEphos [bis(2-diphenylphosphinophenyl)ether]. The catalytic reaction proceeded in DMSO at 80°C and gave a variety of benzylic sulfones in high yields.
