85355-52-8Relevant articles and documents
Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 3443 - 3452 (2008/02/12)
Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzene-disulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts. Georg Thieme Verlag Stuttgart.
An annulative approach to highly substituted indoles: Unusual effect of phenolic additives on the success of the arylation of ketone enolates
Rutherford, Jennifer L.,Rainka, Matthew P.,Buchwald, Stephen L.
, p. 15168 - 15169 (2007/10/03)
A novel palladium-catalyzed arylation of ketone enolates with o-nitrohaloarenes was achieved through the addition of phenol additives. The mild reaction conditions employed allowed for the inclusion of a wide variety of functional groups in both substrates to be tolerated. The products of this reaction were then readily reductively cyclized to give highly substituted indoles in moderate to excellent overall yields. Copyright
Synthesis of Substituted Indoles via Meerwein Arylation
Raucher, Stanley,Koolpe, Gary A.
, p. 2066 - 2069 (2007/10/02)
A new method for the synthesis of substituted indoles is detailed.Meerwein arylation of 4- and 6-substituted 2-nitrobenzenediazonium chlorides with vinyl acetate or vinyl bromide and subsequent reductive cyclization of the resulting adducts affords the corresponding 6- and 4-substituted (CH3, OCH3, Cl, Br, CF3) indoles.The diazonium bisulfates of weakly basic 2-nitroanilines (4-Cl, 6-Br, 4-CF3) gave higher yields of Meerwein arylation adducts than the corresponding diazonium chlorides.Coupling of 2-nitrobenzenediazonium chloride with 2-acetoxy-1-alkenes followed byreductive cyclization affords 2-alkylindoles.