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

A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp2)−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 pr...

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Main Authors:	William A. Nack, Xinmou Wang, Bo Wang, Gang He, Gong Chen
Format:	Article
Language:	English
Published:	Beilstein-Institut 2016-06-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	iodination palladium remote C–H activation tetrahydroquinoline
Online Access:	https://doi.org/10.3762/bjoc.12.119

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spelling	doaj-9c06b0f934cd4dd6977f76834639b88b2021-02-02T00:48:46ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-06-011211243124910.3762/bjoc.12.1191860-5397-12-119Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolinesWilliam A. Nack0Xinmou Wang1Bo Wang2Gang He3Gong Chen4Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United StatesState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, ChinaCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, ChinaDepartment of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United StatesDepartment of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United StatesA new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp2)−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(sp3)−H arylation, Pd-catalyzed ε-C(sp2)−H iodination, and Cu-catalyzed C−N cyclization enables a streamlined synthesis of tetrahydroquinolines bearing diverse substitution patterns.https://doi.org/10.3762/bjoc.12.119iodinationpalladiumremote C–H activationtetrahydroquinoline
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	William A. Nack Xinmou Wang Bo Wang Gang He Gong Chen
spellingShingle	William A. Nack Xinmou Wang Bo Wang Gang He Gong Chen Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines Beilstein Journal of Organic Chemistry iodination palladium remote C–H activation tetrahydroquinoline
author_facet	William A. Nack Xinmou Wang Bo Wang Gang He Gong Chen
author_sort	William A. Nack
title	Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines
title_short	Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines
title_full	Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines
title_fullStr	Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines
title_full_unstemmed	Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines
title_sort	palladium-catalyzed picolinamide-directed iodination of remote ortho-c−h bonds of arenes: synthesis of tetrahydroquinolines
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2016-06-01
description	A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp2)−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(sp3)−H arylation, Pd-catalyzed ε-C(sp2)−H iodination, and Cu-catalyzed C−N cyclization enables a streamlined synthesis of tetrahydroquinolines bearing diverse substitution patterns.
topic	iodination palladium remote C–H activation tetrahydroquinoline
url	https://doi.org/10.3762/bjoc.12.119
work_keys_str_mv	AT williamanack palladiumcatalyzedpicolinamidedirectediodinationofremoteorthochbondsofarenessynthesisoftetrahydroquinolines AT xinmouwang palladiumcatalyzedpicolinamidedirectediodinationofremoteorthochbondsofarenessynthesisoftetrahydroquinolines AT bowang palladiumcatalyzedpicolinamidedirectediodinationofremoteorthochbondsofarenessynthesisoftetrahydroquinolines AT ganghe palladiumcatalyzedpicolinamidedirectediodinationofremoteorthochbondsofarenessynthesisoftetrahydroquinolines AT gongchen palladiumcatalyzedpicolinamidedirectediodinationofremoteorthochbondsofarenessynthesisoftetrahydroquinolines
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Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines

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