Synthesis of Dibenzofurans from Cyclic Diaryliodonium Triflates and Water via Oxygen–Iodine Exchange Approach

Abstract

An efficient synthesis of a variety of dibenzofuran derivatives via Cu-catalyzed cyclization diaryliodonium salts in water is achieved. Various dibenzofuran derivatives could be obtained in good to excellent yields via this oxygen–iodine exchange approach. A concise synthesis of organic semiconducting material molecule has been achieved using this method.

Copper‐Catalyzed One‐Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums

“…The robustness of this protocol was further demonstrated when more congested substrates were successfully transformed into trisubstituted benzofurans ( 2m – 2o ). Recently, a similar strategy with five‐membered CDPIs was also reported by Li group, further confirming that our previous reported oxygenation of five‐membered HCIs could be expanded to CDPIs …”

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

“…Liu et al has also reported a similar strategy to construct diverse dibenzofuran derivatives 63 by reacting five-membered cyclic diaryliodoniums in water. 68 In their publication, several organic semiconducting material scaffolds have been facilitated with moderate yields by further transformations.…”

“…Similarly, five- and six-membered diphenyliodoniums 61′ are compatible with this transformation to provide expected products 63 , while seven-membered and bigger-sized aryliodoniums fail (Scheme ). Liu et al has also reported a similar strategy to construct diverse dibenzofuran derivatives 63 by reacting five-membered cyclic diaryliodoniums in water . In their publication, several organic semiconducting material scaffolds have been facilitated with moderate yields by further transformations.…”

“…Owing to the highly electron-deficient property and unique ring system, cyclic aryliodoniums can be naturally considered to build various polycyclic scaffolds. ,− Such cyclic aryliodonium associated transformations have received increasing interest and made significant advancements. So far, there are a number of reviews on hypervalent iodine­(III). ,,,,,− However, acyclic aryliodoniums and their applications are more focused, ,, for example, Olofsson et al reviewed synthetic developments and applications of acyclic diaryliodonium salts .…”

Easy Access to 2,4-Disubstituted Cyclopentenones by a Gold(III)-Catalyzed A3-Coupling/Cyclization Cascade

“…In continuation of our contributions on gold catalyzed furan syntheses, we recently presented an A3-coupling/cyclization sequence between glyceraldehyde, a secondary amine, and a terminal alkyne that delivered furan alcohol as the product (Scheme , left) . However, during solvent optimization studies for this synthesis of furyl alcohol derivatives, we observed a completely unexpected shift of selectivity by using TFE as solvent.…”