64497-26-3Relevant academic research and scientific papers
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.
Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst
Jin, Ming Yu,Kim, Sun Min,Mao, Hui,Ryu, Do Hyun,Song, Choong Eui,Yang, Jung Woon
supporting information, p. 1547 - 1550 (2014/03/21)
We found that chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio. Moreover, we observed the persistent catalytic activity of the homogeneous NHC catalyst in a solution due to N
A family of thiazolium salt derived N-heterocyclic carbenes (NHCs) for organocatalysis: Synthesis, investigation and application in cross-benzoin condensation
Piel, Isabel,Pawelczyk, Marius D.,Hirano, Keiichi,Froehlich, Roland,Glorius, Frank
supporting information; experimental part, p. 5475 - 5484 (2011/11/29)
A family of thiazolium salt derived N-heterocyclic carbenes (NHCs) bearing sterically demanding aryl substituents on the nitrogen and with varying backbone substitution patterns have been synthesized. Investigation of the catalytic activity of these NHCs in a number of benzoin-type coupling reactions revealed markedly different levels of reactivity and selectivity. To elucidate the underlying factors leading to differences in reactivity, a study of the electronic and steric properties of these NHC catalysts was conducted. By using the best catalyst in this study, the intermolecular cross-benzoin condensation reaction was explored in more detail.
