Regio- and Stereoselective Synthesis of Triarylalkene-Capped Rotaxanes via Palladium-Catalyzed Tandem Sonogashira/Hydroaryl Reaction of Terminal Alkynes

Triarylalkene-capped conjugated rotaxanes were synthesized via a palladium-catalyzed tandem Sonogashira/hydroaryl reaction between aryl halides and terminal alkynes bearing two permethylated α-cyclodextrins (PM α-CDs) with high regioselectivity because of the insulation effect of the PM α-CDs. Moreo...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 82; no. 10; pp. 5449 - 5455
Main Authors Masai, Hiroshi, Matsuda, Wakana, Fujihara, Tetsuaki, Tsuji, Yasushi, Terao, Jun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.05.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
OXIDATION
ALKENES
MECHANISM
ARYL IODIDES
GEOMETRY OPTIMIZATION
YNOL ETHERS
POLYMERIZATION
TETRASUBSTITUTED OLEFINS
HYDROARYLATION
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Summary:Triarylalkene-capped conjugated rotaxanes were synthesized via a palladium-catalyzed tandem Sonogashira/hydroaryl reaction between aryl halides and terminal alkynes bearing two permethylated α-cyclodextrins (PM α-CDs) with high regioselectivity because of the insulation effect of the PM α-CDs. Moreover, sequential Sonogashira coupling and hydroarylation reactions using different aryl substrates afforded a regio- and stereoselective trisubstituted alkene as a single product. This new class of rotaxane-forming reactions can be used to increase the diversity of rotaxane skeletons, and thereby the material functionalities of rotaxanes.
Bibliography:KAKEN
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00442