- The facile and direct formylation of organoboron aromatic compounds with benzodithiolylium tetrafluoroborate
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Organoboron compounds can be used to effect a direct formylation in the absence of transition metals. We report that the direct reaction between boronic derivatives and benzodithiolylium tetrafluoroborate, a commercially available carbenium ionic compound, is possible and provides access to many interesting compounds without the use of transition metals. The direct reaction of the carbenium ion with boronic derivatives results in the formation of substituted arylcarbenium ions, a number of which can be further utilized in materials chemistry or for the direct transformation into other compounds. In addition to the rich chameleonic chemical nature of the benzodithiol intermediate, such species can also undergo a metallation reaction and subsequent treatment with a wide range of electrophiles to access a variety of functional groups (aldehyde, ketone, acid, and alkyl groups). Copyright
- Petruzziello, Diego,Gualandi, Andrea,Jaffar, Hamza,Lopez-Carrillo, Veronica,Cozzi, Pier Giorgio
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p. 4909 - 4917
(2013/08/23)
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- A Convenient Preparation of α-Oxo Ketene Dithioacetals
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The reaction of a series of ketones with 2 equiv. of 1,3-benzodithiolylium tetrafluoroborate affords α-(1,3-benzodithiol-2-ylidene)ketones and 1,3-benzodithiole in good yields.
- Nakayama, Juzo,Sugie, Yasuko,Hoshino, Masamatsu
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p. 939 - 940
(2007/10/02)
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- CONVERSION OF CYCLIC TRITHIOCARBONATES TO THIOACETALS, INCLUDING 1,3-DITHIANE, BY REDUCTION WITH DIISOBUTYLALUMINIUM HYDRIDE (DIBAL)
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Cyclic trithiocarbonates can be desulfurized with diisobutylaluminium hydride (DIBAL) to form the corresponding thioacetals.This new synthetic pathway was exploited for the preparation of several Umpolung reagents, including 1,3-dithiane.An efficient isolation of sodium trithocarbonate is described.
- Jordis, Ulrich,Rudolf, Manfred
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p. 279 - 284
(2007/10/02)
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