- Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis
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An efficient photoredox/nickel catalyzed sulfonylation reaction of aryl, heteroaryl, and vinyl halides has been achieved for the first time. This newly developed sulfonylation protocol provides a versatile method for the synthesis of diverse aromatic sulfones at room temperature and shows excellent functional group tolerance. The electrophilic coupling partners are not limited to aryl, heteroaryl, and vinyl bromides and iodides, but also includes less reactive aryl chlorides as suitable substrates for this transformation.
- Yue, Huifeng,Zhu, Chen,Rueping, Magnus
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supporting information
p. 1371 - 1375
(2018/01/27)
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- Photochemistry of N-Arylsulfonimides: An Easily Available Class of Nonionic Photoacid Generators (PAGs)
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The photochemical behavior of differently substituted N-arylsulfonimides was investigated. Homolysis of the S?N bond took place as the exclusive path from the singlet state to afford both N-arylsulfonamides and photo-Fries adducts, the amount of which depended on reaction conditions and aromatic substituents. Sulfinic and sulfonic acids were released upon irradiation under deaerated and oxygenated conditions, respectively. The nature of the excited states and intermediates involved were proved by laser flash photolysis and EPR experiments. These results highlighted the potential of such compounds as nonionic photoacid generators able to photorelease up to two equivalents of a strong acid for each mole of substrate.
- Torti, Edoardo,Protti, Stefano,Merli, Daniele,Dondi, Daniele,Fagnoni, Maurizio
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supporting information
p. 16998 - 17005
(2016/11/16)
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- Triflic acid–catalyzed rearrangement of unalkylated benzene sulfonanilides
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ABSTRACT: Previous work has demonstrated that alkylated benzene sulfonanilides undergo sulfuric acid (98%)–catalyzed rearrangement to alkylamino diaryl sulfones. Similar treatment of their unalkylated analogs typically leads only to hydrolysis. Surprisingly, when the unalkylated benzene sulfonanilides react with triflic acid, rearrangement to sulfones does occur.
- Newcomer, Rebecca,McKee, James,Zanger, Murray
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supporting information
p. 949 - 955
(2016/07/12)
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- Regioselectivity control of radiation-induced reaction: Electron beam-induced Fries rearrangement of sulfonamide within a β-cyclodextrin inclusion complex
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EB (electron beam) irradiation of sulfonamide within a β-cyclodextrin (β-CD) inclusion complex in the solid state induced the solvent-free Fries rearrangement, which proceeded at a shorter reaction time with reversed regioselectivity by inclusion into the β-CD, compared with that of sulfonamide crystals; the β-CD as a restricted nanospace had a large effect on the reactivity and regioselectivity of the solvent-free EB-Fries rearrangement. The Royal Society of Chemistry 2006.
- Kato, Jun,Kakehata, Hiroyuki,Maekawa, Yasunari,Yamashita, Takashi
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p. 4498 - 4500
(2008/09/19)
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- Electron beam-induced fries rearrangement of sulfonamide and sulfonate crystals
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The electron beam (EB) sensitivity of sulfonic acid derivatives in the crystalline state was much higher than that of the corresponding carboxylic acid derivatives, which was distinct from the results using other energy sources such as heat and UV; especially, sulfonamide derivatives could undergo the chemoselective Fries rearrangement to give ortho and para products in the ratio of ca. 7/3 without the meta isomer. Copyright
- Kato, Jun,Maekawa, Yasunari,Yoshida, Masaru
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p. 266 - 267
(2007/10/03)
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- Photo-Fries rearrangement of N-arylsulfonamides to aminoaryl sulfone derivatives
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Photochemical reaction of variously substituted p-toluenesulfonanilides was studied. The reaction gives rearranged products, o- and p-amino-substituted diaryl sulfones with the combined yields of 38-72%: the p-isomer is more favored over the o-isomer with the selectivity ratio of 1.1-4.3 depending on the substituents. N-Alkylation of the sulfonanilides increases the yields of the rearranged products, and e-withdrawing substituents on the N-phenyl ring does not lower the yields drastically. This study provides simple methodology for the synthesis of o- and p-aminoaryl sulfones which are otherwise not easily accessible.
- Park, Kwanghee Koh,Lee, Jin Joo,Ryu, Jaegyung
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p. 7651 - 7659
(2007/10/03)
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- 5-arylsulfonyl indoles useful for treating disease
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The invention provides derivatives of 5-arylsulfonyl indole and 5-arylsulfonyl indoline compounds which may be in the form of pharmaceutical acceptable salts or compositions that are useful in treating central nervous system diseases such as anxiety and depression. The invention also includes intermediates and processes to make the compounds, isotopically-labeled forms of the compounds and the use of the isotopically labeled forms of the compounds to perform nuclear magnetic resonance imaging and positron emission tomography.
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- Syntheses, absolute configurations, and UV/Vis spectroscopic properties of new chiral tri- and pentamethinium streptocyanine dyes with 4-aminophenyl 4-methylphenyl sulfoxide endgroups
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Starting with monochiral 4-aminophenyl 4-methylphenyl sulfoxides 3a and 3b, the absolute configurations of which were determined by X-ray analysis, we have synthesized the new chiral C2-symmetrical tri- and pentamethinium streptocyanine dyes 5a
- Reichardt, Christian,Erfurt, Hans-Peter,Harms, Klaus,Schaefer, Gerhard
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p. 439 - 452
(2007/10/03)
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