Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 2981-2988Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.316
Keywords
iminium salt; organometallic; oxidative functionalisation; photoredox catalysis; tetrahydroisoquinoline
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Funding
- GlaxoSmithKline
- University of Strathclyde
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Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.
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