A novel, highly modular synthetic method with high functional group tolerance was developed for the construction of chromenoquinoline derivatives from arylpropynyloxy-benzonitriles and diaryliodonium triflates via an oxidative arylation-cyclization path. The copper(I) chloride catalyzed reaction is presumed to involve the formation of highly active arylcopper(III) species.
A novel catalytic method for the direct C-H alkynylation of azulenes is developed. The gold catalyzed functionalization of this special carbacycle is achieved with hypervalent iodonium reagent TIPS-EBX under mild reaction conditions. With the aid of the developed procedure, several TIPS alkynylated azulene derivatives were synthesized bearing important functional groups for further functionalization.
This account aims to give a description of the usefulness of diaryliodonium salts in organic chemistry, including their synthesis and applications in the presence and absence of transition metal catalysts. Herein, we briefly summarize the structural properties and reactivity of diaryliodonium salts. We collected several applications of the hypervalent reagents including metal-free arylations of C, O, N and S nucleophiles. Synthesis and functionalization of aromatic and heteroaromatic systems via copper and palladium catalyzed transformations are also discussed in this account.
Abstract. A novel, highly modular synthetic methodology based on an oxidative arylation-cyclization strategy was developed for the construction of iminobenzoxazine derivatives in the copper-catalyzed reaction of orthocyanoanilides and diaryliodonium salts.
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