Synthesis of 1,2,3,4‐Tetrahydroisoquinolines via Palladium‐Catalyzed Cyclization of N‐Tosylhydrazones with ortho‐Bromophenethyl Tosylamides

A Pd‐catalyzed synthesis of 1,2,3,4‐tetrahydroisoquinoline (THIQ) via cyclization of ortho‐bromophenethyl tosylamides with aryl N‐tosylhydrazones in the presence of base was developed. The reaction is believed to proceed via the oxidative addition of palladium with ortho‐bromophenethyl tosylamides,...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 364; no. 23; pp. 4075 - 4079
Main Authors Zhang, Jieming, Zhang, Zhan‐Ming, Wu, Qi, Zhang, Junliang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.12.2022
Wiley Subscription Services, Inc
Subjects
Aromatic compounds
carbene insertion
Carbenes
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
cyclization
N-tosyl hydrazone
Palladium
Physical Sciences
Science & Technology
tetrahydroisoquinoline
N-tosyl hydrazone
INSERTION
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
NITROGEN-HETEROCYCLES
DIRECT FUNCTIONALIZATION
ISOQUINOLINE ALKALOIDS
carbene insertion
COPPER
cyclization
AMINATION
COUPLING REACTIONS
tetrahydroisoquinoline
CONTAINING HETEROCYCLES
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Summary:A Pd‐catalyzed synthesis of 1,2,3,4‐tetrahydroisoquinoline (THIQ) via cyclization of ortho‐bromophenethyl tosylamides with aryl N‐tosylhydrazones in the presence of base was developed. The reaction is believed to proceed via the oxidative addition of palladium with ortho‐bromophenethyl tosylamides, followed by carbene insertion and cyclization. The carbene species were generated in‐situ from the aryl N‐tosylhydrazones and KOtBu.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200931