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 language | English |
|---|---|
| Pages (from-to) | 3868-3871 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 53 |
| Issue number | 15 |
| DOIs | |
| Publication status | Published - Apr 7 2014 |
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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 journal › Article
}
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 -