36724-16-0Relevant articles and documents
Palladium-Catalyzed Arylthiolation of Alkynes Enabled by Surmounting Competitive Dimerization of Alkynes
Uno, Daisuke,Nogi, Keisuke,Yorimitsu, Hideki
, p. 8295 - 8299 (2019)
By overcoming the unwanted catalytic dimerization of terminal alkynes, palladium-catalyzed carbothiolation of alkynes with heteroaryl sulfides has been accomplished to provide the corresponding β-heteroaryl alkenyl sulfides with high regio- and stereosele
A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
Czyz,Weragoda,Monaghan,Connell,Brzozowski,Scully,Burton,Lupton,Polyzos
supporting information, p. 1543 - 1551 (2018/03/08)
The general catalytic synthesis of aryl and vinyl thioethers from readily available halides remains a challenge. Herein we report a unified method for the thiolation of aryl and vinyl iodides with dialkyl disulfides using visible light photoredox catalysis. A range of thioether products bearing diverse functional groups can be accessed in high yield and with excellent chemoselectivity. We demonstrate the versatility of this method through the expedient synthesis of a family of thioether-rich natural products. A detailed investigation of the photocatalytic mechanism is presented from both steady-state and time-resolved luminescent quenching as well as transient absorption spectroscopy experiments.
Palladium-catalyzed homo-coupling of heteroarylsulfoniums via borylation/Suzuki-Miyaura coupling sequence
Minami, Hiroko,Nogi, Keisuke,Yorimitsu, Hideki
, p. 998 - 1007 (2019/04/26)
Palladium-catalyzed homo-coupling of heteroaryldimethylsulfoniums proceeds in the presence of bis(pinacolato)diboron and a base to yield biheteroaryls. The homo-coupling involves palladium-catalyzed borylation and the subsequent Suzuki-Miyaura coupling. As the sulfoniums were able to be prepared in situ from the corresponding heteroaryl sulfides and methyl triflate, one-pot transformations of heteroaryl sulfides into the homo-coupling products were executed. Furthermore, a facile synthesis of a highly substituted 2,2'-bibenzofuran was accomplished with a combination of Pummerer-type synthesis of 2-benzofuryl sulfide and the present homo-coupling.
Metal-Free Approach to Biaryls from Phenols and Aryl Sulfoxides by Temporarily Sulfur-Tethered Regioselective C-H/C-H Coupling
Yanagi, Tomoyuki,Otsuka, Shinya,Kasuga, Yuko,Fujimoto, Keisuke,Murakami, Kei,Nogi, Keisuke,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, p. 14582 - 14585 (2016/11/18)
We have developed metal-free regiocontrolled dehydrogenative C-H/C-H cross-coupling of aryl sulfoxides with phenols by means of trifluoroacetic anhydride. Because the reaction would proceed through an interrupted Pummerer reaction followed by sulfonium-tethered [3,3]-sigmatropic rearrangement, the C-H/C-H coupling takes place exclusively between the ortho positions of both substrates. Various functional groups including carbonyl, halo, siloxy, and even boryl moieties are compatible. The biaryl products naturally possess hydroxy and sulfanyl groups, which allows the products to be useful synthetic intermediates, as evidenced by the syntheses of π-expanded heteroarenes such as unprecedented 7,12-dioxa[8]helicene.
Nickel-NHC-catalyzed cross-coupling of 2-methylsulfanylbenzofurans with alkyl grignard reagents
Baralle, Alexandre,Otsuka, Shinya,Guérin, Vincent,Murakami, Kei,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, (2015/02/19)
NiCl2(PPh3)(IPr) catalyzes cross-coupling reactions of 2-methylsulfanylbenzofurans with alkyl Grignard reagents. Other nickel complexes such as NiCl2(dppe) failed to catalyze the same reaction. The alkylation is applicable to the synthesis of a couple of protein tyrosine phosphatase inhibitors, 3-(4-biphenylyl)-2-alkylbenzofurans.
4-(2-Hydroxyaryl)-1,2,3-thiadiazoles as a source of 2-benzofuranthiolates
Petrov,Dehaen,Abramov,Abramova,Androsov
, p. 1510 - 1518 (2007/10/03)
Following the Hurd-Mori procedure, 4-(2-hydroxyaryl)-1,2,3-thiadiazoles were synthesized from o-hydroxyacetophenones. Treatment of the products with bases gives 2-benzofuranthiolates which can be involved in alkylation and arylation reactions.
Nucleophilic intramolecular cyclization reactions of alkynechalcogenolates
Abramov,Dehaen,D'Hooge,Petrov,Smeets,Toppet,Voets
, p. 3933 - 3940 (2007/10/03)
2-(ortho-Hydroxyphenyl)-alkynethiolates and -selenolates, obtained through base catalyzed ring cleavage of 4-(ortho-hydroxyphenyl)-1,2,3- thiadiazoles and -1,2,3-selenadiazoles, smoothly transform into 2- benzofuranthiolates and -selenolates. These reactive intermediates can be alkylated in high yield. This reaction sequence could be applied to the synthesis of electron rich thiacrown ethers. The 2-(ortho-aminophenyl)- alkynethiolate analogously forms 2-methylsulfanylindole. (C) 2000 Elsevier Science Ltd.
A general synthesis of benzofuran-2-thiolates via intramolecular addition of phenolates to alkynethiolates
D'Hooge, Bart,Smeets, Stefan,Toppet, Suzanne,Dehaen, Wim
, p. 1753 - 1754 (2007/10/03)
4-(ortho-Hydroxyaryl)-1,2,3-thiadiazoles can be transformed into benzofuran-2-thiolates via an intramolecular cyclization.
An Empirical Aromativcity Index (AIRT) Based on "Reversion to Type" in the Hydrolysis of Methyl Ethers, Methyl Thioethers, and Methyl Selenoethers Derived from Some Heterocyclic and Homocyclic Polyenes
Capon, Brian,Lew, Sing Quan
, p. 7823 - 7838 (2007/10/02)
Hydronium ion catalysed hydrolysis and deuterium exchange in CD3CN-D2O (9:1 v/v) of the following compounds have been investigated: 1-methoxy-, 3-methoxy- and 1-methylthio-cyclohepta-1,3,5-triene, 1-methoxy-cyclooctatetraene, 2-methylthio-, 3-methylthio- and 2-methylseleno-benzofuran, 2-methylthio- and 3-methylthio-benzothiophene, and 2-methylthio-N-methyl-indole.The values of log kex/khyd for these compounds and those of a previous investigation have been used to define an aromaticity scale based on "reversion to type".
