126139-05-7Relevant articles and documents
Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/1,1-Carboxyalkynylation of Alkynylbenziodoxoles
Wu, Junliang,Xu, Kai,Hirao, Hajime,Yoshikai, Naohiko
, p. 1521 - 1525 (2017)
A PdII-catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk-1-en-3-ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd-assisted 1,2-iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups (the latter originating from another molecule of the alkynylbenziodoxole) into the 1-position of the transient Pd-vinylidene species. The product of this 1,1-carboxyalkynylation reaction serves as a new functionalized enyne-type building block for further synthetic transformations.
1,4-Silatropy of S-α-silylbenzyl thioesters: A convenient route to silyl enol and dienol ethers accompanied by C-C bond formation via thiocarbonyl ylides
Choi, Jinil,Imai, Eiichiro,Mihara, Masatoshi,Oderaotoshi, Yoji,Minakata, Satoshi,Komatsu, Mitsuo
, p. 6164 - 6171 (2007/10/03)
A novel convenient method for the generation of thiocarbonyl ylides from readily accessible starting materials and the first synthetic application of in situ generated ylides in the synthesis of silyl enol and dienol ethers, accompanied by C-C bond formation, is described. Under completely neutral conditions without any catalyst or additive, thermal reactions of S-α-silylbenzyl thioesters in sealed tubes at 180 °C provided silyl enol and dienol ethers in good to excellent yields with high stereoselectivities. This procedure consists of a multistep reaction in a one-pot process, i.e., 1,4-silatropy of S-α-silylbenzyl thioesters to give thiocarbonyl ylides, 1,3-electrocyclization of the ylides to give thiiranes, and the extrusion of sulfur from thiiranes to give silyl enol and dienol ethers.
