Metal-Free Arylation of Oxygen Nucleophiles with Diaryliodonium Salts
2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 44, 14140-14149 p.Article in journal (Refereed) Published
Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho-and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy.
Place, publisher, year, edition, pages
2012. Vol. 18, no 44, 14140-14149 p.
aryl esters, arylation, diaryl ethers, hypervalent iodine, synthetic methods
Chemical Sciences Organic Chemistry
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-82958DOI: 10.1002/chem.201201645ISI: 000310473900031OAI: oai:DiVA.org:su-82958DiVA: diva2:576860
FunderSwedish Research Council, 621-2008-3709Carl Tryggers foundation , 08:288Carl Tryggers foundation , 09:281