223801-41-0Relevant academic research and scientific papers
Selective Oxidation of Activated Alcohols by Supported Gold Nanoparticles under an Atmospheric Pressure of O2: Batch and Continuous-Flow Studies
Giorgi, Pascal D.,Elizarov, Nelli,Antoniotti, Sylvain
, p. 1830 - 1836 (2017)
In the hunt for a simple, mild, and scalable protocol for gold nanoparticle-catalyzed oxidation of benzylic and allylic alcohols under O2, we have used commercially available gold nanoparticles supported on alumina to selectively oxidize a large range of activated alcohols to the corresponding carbonyl compounds in good yields (68–99 %) and with excellent selectivity (ca. 100 %). The true heterogeneous nature of the catalysis by gold was demonstrated, allowing us to further adapt this protocol to continuous-flow reactors by using the tube-in-tube technology, in which higher yields were obtained thanks to an improved oxygenation of the reaction medium.
Bicatalytic Multistep Reactions En Route to the One-Pot Total Synthesis of Complex Molecules: Easy Access to Chromene and 1,2-Dihydroquinoline Derivatives from Simple Substrates
Giorgi, Pascal D.,Miedziak, Peter J.,Edwards, Jennifer K.,Hutchings, Graham J.,Antoniotti, Sylvain
, p. 70 - 75 (2017/01/17)
By combining nanocatalysis with base catalysis, a novel one-pot multistep process was found for the synthesis of substituted heterocycles of biological relevance from simple substrates. The process is based on the initial Au/O2 oxidation of allylic alcohols, which is followed by base-catalyzed tandem hetero-Michael/aldolization/crotonization with ortho-hydroxy- or ortho-aminobenzaldehydes. The flexibility of the reaction even allowed the benzaldehyde partner to be prepared in situ in an example of a one-pot/five-step process.
Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling
Shen, Li,Simmons, Charles J.,Sun, Dianqing
, p. 4173 - 4178 (2012/08/28)
Microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling is described. Using the optimized conditions, a panel of macrocycles, with different substitution patterns, ring sizes, and linkers, has been successfully synthesized using microwave irradiation. To the best of our knowledge, this work represents the first examples of the microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling.
Total synthesis and structural revision of engelhardione
Shen, Li,Sun, Dianqing
, p. 4570 - 4574 (2011/09/20)
The total synthesis of the macrocyclic natural product engelhardione is reported. This effort led to the structural revision of the published structure of engelhardione to that of pterocarine. The revision reflects the change of the substitution pattern of one phenyl ether ring from the meta to the para position. To confirm, pterocarine (2) and its close regioisomer 3 were subsequently synthesized for comparison. Moreover, to the best of our knowledge, our synthesis of 1 represents the first example of a 14-membered macrocyclic diarylheptanoid with a meta-meta substitution pattern at the diphenyl ether moiety.
