Iron-catalyzed C(sp2)-H and C(sp3)-H arylation by triazole assistance

Qing Gu, Hamad H. Al Mamari, Karolina Graczyk, Emelyne Diers, Lutz Ackermann

Research output: Contribution to journalArticle

171 Citations (Scopus)

Abstract

Modular 1,2,3-triazoles enabled iron-catalyzed C-H arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp 2)-H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp3)-H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted C-H activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries. With a little help: A versatile iron catalyst allows the arylation of C(sp2)-H and C(sp3)-H bonds in the presence of a modular and removable triazolyldimethylmethyl (TAM) auxiliary, whose structure can be varied through 1,3-dipolar azide-alkyne cycloadditions.

Original languageEnglish
Pages (from-to)3868-3871
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number15
DOIs
Publication statusPublished - Apr 7 2014

Fingerprint

Triazoles
Iron
Catalysts
Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Alkenes
Organometallics
Olefins
Chemical activation

Keywords

  • C-H activation
  • chelation
  • iron
  • ruthenium
  • triazoles

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

Cite this

Iron-catalyzed C(sp2)-H and C(sp3)-H arylation by triazole assistance. / Gu, Qing; Al Mamari, Hamad H.; Graczyk, Karolina; Diers, Emelyne; Ackermann, Lutz.

In: Angewandte Chemie - International Edition, Vol. 53, No. 15, 07.04.2014, p. 3868-3871.

Research output: Contribution to journalArticle

Gu, Qing ; Al Mamari, Hamad H. ; Graczyk, Karolina ; Diers, Emelyne ; Ackermann, Lutz. / Iron-catalyzed C(sp2)-H and C(sp3)-H arylation by triazole assistance. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 15. pp. 3868-3871.
@article{e5a4dcb2c5794a329ca0b164a3411b45,
title = "Iron-catalyzed C(sp2)-H and C(sp3)-H arylation by triazole assistance",
abstract = "Modular 1,2,3-triazoles enabled iron-catalyzed C-H arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp 2)-H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp3)-H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted C-H activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries. With a little help: A versatile iron catalyst allows the arylation of C(sp2)-H and C(sp3)-H bonds in the presence of a modular and removable triazolyldimethylmethyl (TAM) auxiliary, whose structure can be varied through 1,3-dipolar azide-alkyne cycloadditions.",
keywords = "C-H activation, chelation, iron, ruthenium, triazoles",
author = "Qing Gu and {Al Mamari}, {Hamad H.} and Karolina Graczyk and Emelyne Diers and Lutz Ackermann",
year = "2014",
month = "4",
day = "7",
doi = "10.1002/anie.201311024",
language = "English",
volume = "53",
pages = "3868--3871",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "15",

}

TY - JOUR

T1 - Iron-catalyzed C(sp2)-H and C(sp3)-H arylation by triazole assistance

AU - Gu, Qing

AU - Al Mamari, Hamad H.

AU - Graczyk, Karolina

AU - Diers, Emelyne

AU - Ackermann, Lutz

PY - 2014/4/7

Y1 - 2014/4/7

N2 - Modular 1,2,3-triazoles enabled iron-catalyzed C-H arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp 2)-H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp3)-H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted C-H activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries. With a little help: A versatile iron catalyst allows the arylation of C(sp2)-H and C(sp3)-H bonds in the presence of a modular and removable triazolyldimethylmethyl (TAM) auxiliary, whose structure can be varied through 1,3-dipolar azide-alkyne cycloadditions.

AB - Modular 1,2,3-triazoles enabled iron-catalyzed C-H arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp 2)-H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp3)-H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted C-H activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries. With a little help: A versatile iron catalyst allows the arylation of C(sp2)-H and C(sp3)-H bonds in the presence of a modular and removable triazolyldimethylmethyl (TAM) auxiliary, whose structure can be varied through 1,3-dipolar azide-alkyne cycloadditions.

KW - C-H activation

KW - chelation

KW - iron

KW - ruthenium

KW - triazoles

UR - http://www.scopus.com/inward/record.url?scp=84898064300&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84898064300&partnerID=8YFLogxK

U2 - 10.1002/anie.201311024

DO - 10.1002/anie.201311024

M3 - Article

C2 - 24596034

AN - SCOPUS:84898064300

VL - 53

SP - 3868

EP - 3871

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 15

ER -