Iodination of remote ortho-C-H bonds of arenes via directed S EAr: A streamlined synthesis of tetrahydroquinolines

William A. Nack; Gang He; Shu Yu Zhang; Chengxi Lu; Gong Chen

doi:10.1021/ol4015078

Iodination of remote ortho-C-H bonds of arenes via directed S _EAr: A streamlined synthesis of tetrahydroquinolines

William A. Nack, Gang He, Shu Yu Zhang, Chengxi Lu, Gong Chen

Chemistry

Research output: Contribution to journal › Article › peer-review

43 Scopus citations

Abstract

A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp³)-H arylation, metal-free ε-C(sp²)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.

Original language	English (US)
Pages (from-to)	3440-3443
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	13
DOIs	https://doi.org/10.1021/ol4015078
State	Published - Jul 5 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol4015078

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abstract = "A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp3)-H arylation, metal-free ε-C(sp2)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.",

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AU - He, Gang

AU - Zhang, Shu Yu

AU - Lu, Chengxi

AU - Chen, Gong

PY - 2013/7/5

Y1 - 2013/7/5

N2 - A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp3)-H arylation, metal-free ε-C(sp2)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.

AB - A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp3)-H arylation, metal-free ε-C(sp2)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.

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JF - Organic Letters

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Iodination of remote ortho-C-H bonds of arenes via directed S _EAr: A streamlined synthesis of tetrahydroquinolines

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