Chemoselectivity Investigation on Arylations Using Diaryliodonium Salts

Chemoselectivity Investigation on Arylations Using Diaryliodonium Salts

Malmgren, Joel; Jalalian, Nazli; Olofsson, Berit

Abstract:

Arylations are important transformations in organic synthesis. Aryl ethers, aryl esters and a-aryl carbonyl compounds are important substructures in a variety of compounds such as pharmaceuticals and natural products. Diaryliodonium salts have recently been recognized as versatile reagents in organic synthesis. They can be employed both in metal mediated and metal-free reactions thereby avoiding the potential drawbacks of organometallic chemistry such as toxicity and high cost. Efficient one-pot procedures to diaryliodonium salts have been developed within our group (Scheme 1) increasing the availability of these compounds. With fast and non-expensive procedures for the preparation of these salts in hand we are currently investigating the electrophilic arylating potential of these reagents. The results from a chemoselectivity investigation where different nucleophiles have been arylated using unsymmetric salts are presented.

Arylations are important transformations in organic synthesis. Aryl ethers, aryl esters and a-aryl carbonyl compounds are important substructures in a variety of compounds such as pharmaceuticals and natural products. Diaryliodonium salts have recently been recognized as versatile reagents in organic synthesis. They can be employed both in metal mediated and metal-free reactions thereby avoiding the potential drawbacks of organometallic chemistry such as toxicity and high cost. Efficient one-pot procedures to diaryliodonium salts have been developed within our group (Scheme 1) increasing the availability of these compounds. With fast and non-expensive procedures for the preparation of these salts in hand we are currently investigating the electrophilic arylating potential of these reagents. The results from a chemoselectivity investigation where different nucleophiles have been arylated using unsymmetric salts are presented.

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DOI: 10.5151/chempro-14bmos-R0265-1

Referências bibliográficas

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Como citar:

Malmgren, Joel; Jalalian, Nazli; Olofsson, Berit; "Chemoselectivity Investigation on Arylations Using Diaryliodonium Salts", p-265-265. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0265-1