Palladium-catalyzed alkoxycarbonylation of aryl- and alkenyl-iodonium salts

Kang, Suk‐Ku; Yamaguchi, Tokutaro; Ho, Pil‐Su; Kim, Won-Yeob; Ryu, Hyung-Chul

doi:10.1039/a800209f

Cited by 31 publications

(19 citation statements)

References 14 publications

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“…[20] Pd-catalyzed oxidative coupling of phenols with aromatic aldehydes or benzylic alcohols [21] or carbonylative coupling with aryl halides also deliver aryl esters. [22] Aryl acetates can be synthesized by CÀH activation of arenes with internal directing groups. [23] As part of our long-term interest in the synthesis [24] and application [25] of hypervalent iodine compounds as selective and environmentally benign reagents, [16a, 26] we have examined the arylation of oxygen nucleophiles with diaryliodonium salts.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Arylation of Oxygen Nucleophiles with Diaryliodonium Salts

Jalalian

Petersen

Olofsson

2012

Chemistry A European J

154

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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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Section: Introductionmentioning

confidence: 99%

Metal‐Free Arylation of Oxygen Nucleophiles with Diaryliodonium Salts

Jalalian

Petersen

Olofsson

2012

Chemistry A European J

154

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“…[16] To get more insight into the mechanism, we performed some control experiments (Scheme 3). [14] These outcomes indicated that, unlike our previously reported iodine(III)-mediated alkene activation process,t he arylcarbonylation reaction might proceed through initial palladium oxidation by the DAIS to generate both Ar L Pd II and Ar S Pd II species; [6e] the weakly Lewis acidic DAIS presumably could not activate alkenes. (2)].…”

Section: Angewandte Chemiementioning

confidence: 84%

“…Zuschriften did not bear an ortho substituent gave only atrace amount of arylcarbonylation products,i nstead direct arylation occurred to give ArCO 2 Me as the major product [14] (see the Supporting Information). Notably,o ur arylcarbonylation reaction could be conducted in ao ne-pot fashion by directly using bulky arenes (Ar L H)a sa rylation reagents.F or example,d iaryliodonium salt 2acould be generated in situ from commercially available PhI(OAc) 2 and mesitylene, [7a, 15] and was further treated with alkene 1b to afford the arylcarbonylated product 3b in 85 % yield [Eq.…”

Section: Angewandte Chemiementioning

confidence: 99%

Palladium‐Catalyzed Intermolecular Arylcarbonylation of Unactivated Alkenes: Incorporation of Bulky Aryl Groups at Room Temperature

Chen

Liu

2018

Angewandte Chemie

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Apalladium-catalyzed intermolecular arylcarbonylation of unactivated alkenes has been developed. Unsymmetrical diaryliodonium salts (DAISs) were used as arylation reagents,t he bulkya ryl group (Ar L )o fw hich was exclusively incorporated into the arylcarbonylated products,w hich contained the Ar L group and acarboxylic ester group at the a-and b-carbon position, respectively,o ft he original terminal CÀC double bond. The reaction features excellent chemo-and regioselectivity,high functional-group tolerance,and very mild reaction conditions. Scheme 1. Transition-metal-catalyzed arylation of alkenes with unsymmetrical DAISs.

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“…Iodonium salt 1 also showed high reactivity towards the palladium-catalyzed carbonylation reaction (Scheme 4). [7] The reaction with atmospheric carbon monoxide and triethylamine in methanol at 60 8C was completed within 5 min to give an 86% yield of 2-iodo-2'-methoxycarbonyl-1,1'-binaphthyl 6. The second carbonylation giving diester was not observed at all.…”

Section: Resultsmentioning

confidence: 99%

“…Diaryliodonium salts [4] attracted our attention, because the carbon-iodonium bond is known to undergo oxidative addition to palladium(0) and hence they are reactive substrates for some of the typical palladium-catalyzed reactions, for example, cross-coupling, [5] Heck, [6] and carbonylation. [7] Herein we report the use of the dinaphthaleneiodonium salt 1 for palladium-catalyzed reactions, which provides a new route to 2-substituted 1,1'-binaphthyls containing iodide at the 2' position.…”

Section: Introductionmentioning

confidence: 99%