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Palladium-catalyzed picolinamide-directed iodination of remote ortho-C-H bonds of arenes: Synthesis of tetrahydroquinolines.

ABSTRACT: A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ?-C(sp(2))-H bonds of ?-arylpropylamine substrates is reported. This reaction proceeds selectively with a variety of ?-arylpropylamines bearing strongly electron-donating or withdrawing substituents, complementing our previously reported PA-directed electrophilic aromatic substitution approach to this transformation. As demonstrated herein, a three step sequence of Pd-catalyzed ?-C(sp(3))-H arylation, Pd-catalyzed ?-C(sp(2))-H iodination, and Cu-catalyzed C-N cyclization enables a streamlined synthesis of tetrahydroquinolines bearing diverse substitution patterns.

SUBMITTER: Nack WA

PROVIDER: S-EPMC4979757 | biostudies-other | 2016

REPOSITORIES: biostudies-other

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Palladium-catalyzed picolinamide-directed iodination of remote ortho-C-H bonds of arenes: Synthesis of tetrahydroquinolines.

Nack William A WA Wang Xinmou X Wang Bo B He Gang G Chen Gong G

Beilstein journal of organic chemistry 20160617

A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp(2))-H bonds of γ-arylpropylamine substrates is reported. This reaction proceeds selectively with a variety of γ-arylpropylamines bearing strongly electron-donating or withdrawing substituents, complementing our previously reported PA-directed electrophilic aromatic substitution approach to this transformation. As demonstrated herein, a three step sequence of Pd-catalyzed γ-C(sp(3))-H arylation, Pd-catalyzed ...[more]

PMID: 27559375

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