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

Research output: Contribution to journalArticle

31 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3440-3443
Number of pages4
JournalOrganic Letters
Volume15
Issue number13
DOIs
StatePublished - Jul 5 2013

Fingerprint

Halogenation
cross coupling
Iodides
synthesis
iodides
Amines
amines
Substitution reactions
Metals
substitutes
metals
1,2,3,4-tetrahydroquinoline
picolinamide

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Nack, William A. ; He, Gang ; Zhang, Shu Yu ; Lu, Chengxi ; Chen, Gong. / Iodination of remote ortho-C-H bonds of arenes via directed S EAr : A streamlined synthesis of tetrahydroquinolines. In: Organic Letters. 2013 ; Vol. 15, No. 13. pp. 3440-3443.
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Iodination of remote ortho-C-H bonds of arenes via directed S EAr : A streamlined synthesis of tetrahydroquinolines. / Nack, William A.; He, Gang; Zhang, Shu Yu; Lu, Chengxi; Chen, Gong.

In: Organic Letters, Vol. 15, No. 13, 05.07.2013, p. 3440-3443.

Research output: Contribution to journalArticle

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