Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study

Autor:	Stefano Santoro, Fahmi Himo, Berit Olofsson, Nazli Jalalian, Joel Malmgren
Rok vydání:	2013
Předmět:	Organisk kemi Reaction mechanism Aryl Organic Chemistry General Chemistry Full Papers hypervalent compounds DFT calculations Combinatorial chemistry Catalysis ligand exchange chemistry.chemical_compound Nucleophile chemistry chemoselectivity Reagent Moiety Organic chemistry arylation Phenols Chemoselectivity
Zdroj:	Chemistry (Weinheim an Der Bergstrasse, Germany)
ISSN:	0947-6539
DOI:	10.1002/chem.201300860
Popis:	Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new "anti-ortho effect" has been identified in the arylation of malonates. Several "dummy groups" have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents.
Databáze:	OpenAIRE
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