Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant
Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 % catalyst loading, up to 99 % yield) and broad substrate scope (various alkynes, inter- and intramolecular fashion). The gold(I) catalyst acts as both a π-acid for alkyne activation and a redox catalyst for AuI/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant.
Wang, Jin,Zhang, Shuyao,Xu, Chang,Wojtas, Lukasz,Akhmedov, Novruz G.,Chen, Hao,Shi, Xiaodong
supporting information
p. 6915 - 6920
(2018/05/14)
Stereoselective Addition Reaction of Allylic Sulfides to Acetylenic Esters: E/Z Stereochemical Variations by Lewis Acid
The Lewis acid catalyzed addition reactions of allylic sulfides to methyl propiolate (MP) and dimethyl acetylenedicarboxylate (DMAD) have been investigated.The stereochemical outcome is considerably influenced by the Lewis acid.While the AlCl3-catalyzed r
Hayakawa, Kenji,Kamikawaji, Yoshimasa,Wakita, Akemi,Kanematsu, Ken
p. 1985 - 1989
(2007/10/02)
ALUMINIUM-CHLORIDE CATALYZED REACTION OF ALLYLIC SULFIDES WITH METHYL PROPIOLATE: A NOVEL ADDITION REACTION VIA AN IONIC SIGMATROPIC REARRANGEMENT
The aluminium-chloride catalyzed reaction of allylic sulfides with methyl propiolate resulted in the clean formation of novel 1:1 adducts via ionic sigmatropic rearrangements.
Hayakawa, Kenji,Kamikawaji, Yoshimasa,Kanematsu, Ken
p. 2171 - 2174
(2007/10/02)
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