Combining Bidentate Lewis Acid Catalysis and Photochemistry: Formal Insertion of o-Xylene into an Enamine Double Bond | Zendy

Sebastian Ahles | Zendy; Julia Ruhl | Zendy; Marcel A. Strauss | Zendy; Hermann A. Wegner | Zendy

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Combining Bidentate Lewis Acid Catalysis and Photochemistry: Formal Insertion of o-Xylene into an Enamine Double Bond

Author(s) -

Sebastian Ahles,

Julia Ruhl,

Marcel A. Strauss,

Hermann A. Wegner

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b01020

Subject(s) - enamine , chemistry , lewis acids and bases , double bond , catalysis , cyclobutanes , denticity , medicinal chemistry , organic chemistry , cycloaddition , crystal structure

A bidentate Lewis acid catalyzed domino inverse-electron-demand Diels-Alder reaction combined with a photoinduced ring opening formally inserts o-xylene moieties into enamine double bonds. After reduction, phenethylamines were obtained in good yields. The scope of the reaction was determined by variation of all three starting compounds: phthalazines, aldehydes, and amines.

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