- Temperature-Controlled Chemoselective Synthesis of Thiosulfonates and Thiocyanates: Novel Reactivity of KXCN (X=S, Se) towards Organosulfonyl Chlorides
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An efficient chemoselective protocol has been developed for the synthesis of thiosulfonates and thiocyanates by employing cost effective and commercially available organosulfonyl chlorides with potassium thio-/selenocyanate. The strategy offered the thiosulfonates and thiocyanates selectively by tuning the equivalents of KSeCN and optimizing the reaction temperature. On the other hand, thiosulfonates were obtained as sole products when organosulfonyl chlorides were treated with KSCN. Furthermore, the syntheses of diarylthioethers and aryl(heteroaryl) thioethers were carried out as a part of synthetic application of newly prepared arylthiocyanates.
- Kalaramna, Pratibha,Goswami, Avijit
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supporting information
p. 5359 - 5366
(2021/10/25)
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- One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)
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An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.
- Xu, Lijun,Wang, Hongyu,Zheng, Changwu,Zhao, Gang
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p. 6057 - 6066
(2017/09/23)
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- Transition-metal-free synthesis of thiocyanato- or nitro-arenes through diaryliodonium salts
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A transition-metal-free approach to facile synthesis of thiocyanato- and nitro-arenes was developed from KSCN (potassiumthiocyanate) or NaNO2with diaryliodonium salts in good yields under mild conditions. The reaction was compatible with a variety of sensitive functional substituents such as halides and nitro and ester groups. The usefulness of arylation products has been realized. (Formula Present).
- Li, Xiao-Hua,Li, Liang-Gui,Mo, Xue-Ling,Mo, Dong-Liang
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supporting information
p. 963 - 970
(2016/07/07)
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- A mild copper-catalyzed aerobic oxidative thiocyanation of arylboronic acids with TMSNCS
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A facile and efficient transformation of arylboronic acids to their corresponding aryl thiocyanates has been successfully developed. Based on the CuCl-catalyzed oxidative cross-coupling reaction between arylboronic acids and trimethylsilylisothiocyanate (TMSNCS) under oxygen atmosphere, the transformation can be readily conducted at ambient temperature. The newly-developed protocol provided a competitive synthetic approach to aryl thiocyanates that can tolerate a broad range of reactive functional groups and/or strong electron-withdrawing groups.
- Sun, Nan,Che, Liusheng,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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supporting information
p. 691 - 696
(2015/02/19)
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- General and practical formation of thiocyanates from thiols
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A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.
- Frei, Reto,Courant, Thibaut,Wodrich, Matthew D.,Waser, Jerome
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supporting information
p. 2662 - 2668
(2015/02/05)
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- Synthesis of aryl thiocyanates via copper-catalyzed aerobic oxidative cross-coupling between arylboronic acids and KSCN
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A new protocol for the preparation of aryl thiocyanates by the cross-coupling reaction of arylboronic acids with KSCN salt is described. The coupling reaction was catalyzed by 20 mol% of copper acetate in the presence of 2.0 equivalents 4-methylpyridine serving both as ligand and base under 0.2 MPa of molecular oxygen. A variety of arylboronic acids, including those with substituents at ortho position, were suitable under the reaction conditions. Georg Thieme Verlag Stuttgart · New York.
- Sun, Nan,Zhang, Han,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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supporting information
p. 1443 - 1447
(2013/07/26)
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- Syntheses of Organic N,N-Dialkyldithiocarbamates or Organic Thiocyanates from Organozincs and Corresponding Thio-Anions via the Inversion of Electronic Reactivity of the Anions with NCS-Oxidation
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Novel displacement of metal ions from organometallic compounds with nucleophilic reagents was achieved in the reaction between organozinc compounds and N,N-dialkyldithiocarbamate ions (N,N-DAD-) or thiocyanate ion by the assistance of NCS, whereby alkyl or aryl N,N-DAD or alkyl, alkenyl, alkynyl, aryl, or heteroaryl thiocyanates were obtained in moderate to excellent yields as the result of novel bond construction between carbon fragments from organozinc compounds and thio-anions.
- Takagi, Kentaro,Takachi, Hideaki,Sasaki, Ken
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p. 6552 - 6556
(2007/10/03)
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- Facile Synthesis of Organic Thiocyanates from Organozinc(II) Thiocyanates and N-chlorosuccinimide
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The reaction of organozinc(II) compounds, generated in situ from organolithiums and zinc(II) thiocyaniate, with N-chlorosuccinimide (NCS) afforded the corresponding organic thiocyanates in good yields.
- Takagi, Kentaro,Takachi, Hideaki,Hayama, Naomi
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p. 509 - 510
(2007/10/02)
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