41049-36-9Relevant articles and documents
The Direct Conversion of α-Hydroxyketones to Alkynes
Ghiringhelli, Francesca,Nattmann, Lukas,Bognar, Sabine,Van Gemmeren, Manuel
, p. 983 - 993 (2019/01/24)
Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.
Aerobic oxidative iodination of ketones catalysed by sodium nitrite "on water" or in a micelle-based aqueous system
Stavber, Gaj,Iskra, Jernej,Zupan, Marko,Stavber, Stojan
scheme or table, p. 1262 - 1267 (2010/05/02)
Selective and efficient aerobic oxidative iodination of ketones in aqueous media was achieved by using molecular iodine as the source of iodine atoms, air as the terminal oxidant, sodium nitrite (NaNO2) as the catalyst and H2SO4
Complete switch of migratory aptitude in aluminum-catalyzed 1,2-rearrangement of differently α,α-disubstituted a-siloxy aldehydes
Ohmatsu, Kohsuke,Tanaka, Takayuki,Ooi, Takashi,Maruoka, Keiji
supporting information; experimental part, p. 5203 - 5206 (2009/04/11)
(Chemical Equation Presented) Control of the migration tendency: The regiodivergent 1,2-rearrangement of asiloxy aldehydes bearing α-aryl and α-alkyl substituents into α-siloxy ketones has been realized by using different aluminum Lewis acid catalyst/solvent systems (see scheme). The scope of this unprecedented protocol has been investigated with various substrates and clearly demonstrates its utility for the selective synthesis of two structural isomers from one substrate.
