Decatungstate Photocatalyzed Benzylation of Alkenes with Alkylaromatics. Issue 14 (9th October 2013)

• Record Type: Journal Article
• Authors: Qrareya, Hisham; Ravelli, Davide; Fagnoni, Maurizio; Albini, Angelo
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 14/15(2013)
• Page Start: 2891
• Page End: 2899
• Publication Date: 2013-10-09
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300598
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The direct benzylation of electrophilic alkenes with alkylbenzenes has been achieved by decatungstate photocatalysis in a high ionic strength medium (5:1 acetonitrile/water mixed solvents, 0.5 M lithium perchlorate). The reaction has been extended to ring‐substituted (Cl, F, CN) toluenes and further alkylbenzenes. Intramolecular selectivity (<italic>p</italic>‐cymene, 4‐methylanisole) and deuteration effects support the atom transfer character of the process that, however, requires a sufficient stabilization of the intermediate polar exciplex to occur. The reactivity of the decatungstate anion is compared with that of aromatic ketones, the benchmark of photochemical hydrogen/electron transfer processes.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t3826pd" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>