1284218-97-8Relevant academic research and scientific papers
Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
Roscales, Silvia,Csáky, Aurelio G.
supporting information, p. 8728 - 8732 (2021/03/16)
A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.
[3,3]-sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: Synthesis of substituted 2-indanones and indenes
Tudjarian, Armen A.,Minehan, Thomas G.
supporting information; experimental part, p. 3576 - 3581 (2011/06/25)
Substituted benzyl alkynyl ethers, prepared from the corresponding α-alkoxy ketones in a two-step sequence involving enol triflate formation and KOtBu-induced E2 elimination, undergo [3,3]-sigmatropic rearrangement/ intramolecular 5-exo-dig cyclization at 60 °C to form substituted 2-indanones in good overall yields. 1,3-cis-Disubstituted-2-indanones are formed preferentially when the benzylic substituent R1 is bulky. Substituted indenes may be prepared from 2-indanones in high yields by Horner-Wadsworth-Emmons reaction.
