Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

Triorganoindium reagents (R3In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph3CBF4 as an oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion int...

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Published inJournal of organic chemistry Vol. 84; no. 15; pp. 9778 - 9785
Main Authors Gil-Negrete, José M, Pérez Sestelo, José, Sarandeses, Luis A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.08.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
APORPHINE ALKALOIDS
ASYMMETRIC-SYNTHESIS
INDIUM ORGANOMETALLICS
TERTIARY-AMINES
ALLYLATION
CHEMISTRY
H BOND ARYLATION
EFFICIENT
DERIVATIVES
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Summary:Triorganoindium reagents (R3In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph3CBF4 as an oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion intermediate, supporting a two-step mechanism based on THIQ oxidation and R3In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid nuciferine in three steps.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00928