- B(C6F5)3- And HB(C6F5)2-mediated transformations of isothiocyanates
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This contribution reports on the reactivity of isothiocyanates towards the boranes B(C6F5)3and HB(C6F5)2. The reactions of alkyl-substituted isothiocyanates with B(C6F5)3were found to result in rearrangement reactions to yield stable thiocyanate-B(C6F5)3adducts. Treatment of isothiocyanates with HB(C6F5)2leads to 1,2-hydroboration and thus, B,N,C,S heterocycles are formed, which react further under non-inert conditions. Hydrolysis of the hydroboration products leads to a new access to thioformamides.
- Fischer, Malte,Schmidtmann, Marc
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p. 6205 - 6208
(2020/06/22)
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- Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent
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Thioformamides are easily prepared-under full chemocontrol-through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent. The high electrophilicity of the starting materials enables the straightforward addition of the hydride ion, thus constituting a reliable and high-yielding method for obtaining variously functionalized thioformamides. Sensitive chemical groups to the reduction conditions such as nitro, ester, alkene, azo, azide and keto groups do not interfere with the chemoselectivity of the process. Moreover, the stereochemical information embodied in the starting material is fully retained in the final products. The synthetic potential of the selected thioformamide template is also briefly discussed.
- De La Vega-Hernández, Karen,Senatore, Raffaele,Miele, Margherita,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
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supporting information
p. 1970 - 1978
(2019/02/20)
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- A new convenient synthesis of 5-aryl-2-(arylamino)-1,3,4-oxadiazole derivatives
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Electrical energy offers numerous benefits for conducting a synthesis, including increased reaction rates, yield enhancements and cleaner chemistries. 5-Aryl-2-(arylamino)-1,3,4-oxadiazoles were synthesized directly from acylthiosemicarbazide on the plati
- Kumar, Sanjeev
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body text
p. 216 - 220
(2012/08/29)
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- Synthesis of O-ethyl thioformate: A useful reagent for the thioformylation of amines
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O-Ethyl thioformate has been synthesized from triethylorthoformate and hydrogen sulfide gas using a Bronstead acid catalyst. The product can be isolated as a neat liquid in 83% overall yield. Both the crude and purified thiolate can be used to thioformylate a variety of amines in good to excellent yields.
- Borths, Christopher J.,Chan, Johann,Burke, Brenda J.,Larsen, Robert D.
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experimental part
p. 3139 - 3142
(2010/03/24)
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- Novel reduction of isothiocyanates to thioformamides with SmI2 and tert-butyl alcohol in the presence of HMPA
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Isocyanates react with SmI2 and tert-butyl alcohol in the presence of HMPA to give thioformamides in excellent yields under mild conditions.
- Park, Heui Sul,Lee, In Sang,Kim, Yong Hae
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p. 1805 - 1806
(2007/10/03)
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- Reactions of (C5Me5)Rh(PMe3)(R)H with electrophiles. Insertion of unsaturated molecules into activated carbon-hydrogen bonds
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Earlier studies have shown that the intermediate [C5Me5)Rh(PMe3)] reacts with both alkane and arene C-H bonds to give oxidative-addition adducts. In this paper, reactions of electrophiles with complexes of the type (C5Me5)Rh(PMe3)(R)H, where R = methyl, phenyl, and 2,6-xylyl, are discussed. While insertion into the metal-hydrogen bond results in the formation of a stable functionalized metal complex containing the alkane or arene, elimination of organic products is found to proceed only under oxidizing conditions.
- Jones,Chandler,Feher
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p. 164 - 174
(2008/10/08)
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