70445-86-2Relevant academic research and scientific papers
Transition-Metal-Free Synthesis of C3-Arylated Benzofurans from Benzothiophenes and Phenols
Yang, Kevin,Pulis, Alexander P.,Perry, Gregory J. P.,Procter, David J.
, p. 7498 - 7503 (2018)
We report a transition-metal-free synthesis of benzofurans from benzothiophenes and phenols that exploits the unique reactivity of sulfoxides. Through a sequence involving an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement, phenols can b
Para-coupling of phenols with C2/C3-substituted benzothiophene S-oxides
He, Zhen,Biremond, Tony,Perry, Gregory J.P.,Procter, David J.
supporting information, (2020/06/17)
C2 and C3 substituted benzothiophenes are common structures in medicinal and materials chemistry. The cross-coupling of phenols with benzothiophenes is a useful route towards these important molecules. In this report we reveal an efficient C–H/C–H-type cross-coupling of benzothiophenes, activated as their S-oxides, with phenols to give C2/C3 arylated benzothiophenes. Whereas previous reports describe cross-coupling at the ortho-position between phenols and sulfoxides, this procedure allows para-functionalization of phenols that typically have their ortho positions blocked.
Transition-Metal-Free Cross-Coupling of Benzothiophenes and Styrenes in a Stereoselective Synthesis of Substituted (E,Z)-1,3-Dienes
?iau?iulis, Mindaugas,Ahlsten, Nanna,Pulis, Alexander P.,Procter, David J.
supporting information, p. 8779 - 8783 (2019/06/19)
A transition metal-free one-pot stereoselective approach to substituted (E,Z)-1,3-dienes was developed by using an interrupted Pummerer reaction/ligand-coupling strategy. Readily available benzothiophene S-oxides, which can be conveniently prepared by oxidation of the parent benzothiophenes, undergo Pummerer coupling with styrenes. Reaction of the resultant sulfonium salts with alkyllithium/magnesium reagents generates underexploited hypervalent sulfurane intermediates that undergo selective ligand coupling, resulting in dismantling of the benzothiophene motif and the formation of decorated (E,Z)-1,3-dienes.
