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Metal-Free Arylatio...
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Jalalian, NazliStockholms universitet,Institutionen för organisk kemi
(author)
Metal-Free Arylation of Oxygen Nucleophiles with Diaryliodonium Salts
- Article/chapterEnglish2012
Publisher, publication year, extent ...
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2012-09-27
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Wiley,2012
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Numbers
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LIBRIS-ID:oai:DiVA.org:su-82958
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https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-82958URI
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https://doi.org/10.1002/chem.201201645DOI
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Language:English
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Summary in:English
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Subject category:ref swepub-contenttype
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Subject category:art swepub-publicationtype
Notes
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AuthorCount:3;
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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.
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Petersen, Tue B.Stockholms universitet,Institutionen för organisk kemi
(author)
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Olofsson, BeritStockholms universitet,Institutionen för organisk kemi(Swepub:su)beolo
(author)
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Stockholms universitetInstitutionen för organisk kemi
(creator_code:org_t)
Related titles
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In:Chemistry - A European Journal: Wiley18:44, s. 14140-141490947-65391521-3765
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