705254-34-8Relevant articles and documents
Refining boron-iodane exchange to access versatile arylation reagents
Karandikar, Shubhendu S.,Stuart, David R.
supporting information, p. 1211 - 1214 (2022/02/03)
Aryl(Mes)iodonium salts, which are multifaceted aryl transfer reagents, are synthesized via boron-iodane exchange. Modification to both the nucleophilic (aryl boron) and electrophilic (mesityl-λ3-iodane) reaction components results in improved yield and faster reaction time compared to previous conditions. Mechanistic studies reveal a pathway that is more like transmetallation than SEAr.
The facile and direct formylation of organoboron aromatic compounds with benzodithiolylium tetrafluoroborate
Petruzziello, Diego,Gualandi, Andrea,Jaffar, Hamza,Lopez-Carrillo, Veronica,Cozzi, Pier Giorgio
, p. 4909 - 4917 (2013/08/23)
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
Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid
Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.,Dreher, Spencer D.,Tudge, Matthew T.
supporting information; experimental part, p. 11667 - 11673 (2012/09/05)
The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.
