Details
| Original language | English |
|---|---|
| Pages (from-to) | 4979-4989 |
| Number of pages | 11 |
| Journal | Organometallics |
| Volume | 36 |
| Issue number | 24 |
| Publication status | Published - 14 Dec 2017 |
Abstract
The iron-catalyzed directed ortho-functionalization of arenes developed to an important method in the field of C-H activation. On the other hand, the iron-catalyzed ortho-functionalization of ferrocenes bearing ortho-directing groups (ODGs) has scarcely been investigated. Herein we present the iron-catalyzed ortho-alkylation and -arylation of ODG-substituted ferrocenes bearing a bidentate ODG with the formation of racemic 1,2-disubstituted ferrocenes in up to 94% yield. The approach toward an enantioselective iron-catalyzed C-H activation resulted in an ortho-phenylation with a promising enantiomeric excess of 46%. The first iron-catalyzed diastereoselective ortho-methylation gave an excellent diastereomeric excess of ≥99%.
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
- Chemistry(all)
- Inorganic Chemistry
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In: Organometallics, Vol. 36, No. 24, 14.12.2017, p. 4979-4989.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Directed Iron-Catalyzed ortho-Alkylation and Arylation
T2 - Toward the Stereoselective Catalytic Synthesis of 1,2-Disubstituted Planar-Chiral Ferrocene Derivatives
AU - Schmiel, David
AU - Butenschön, Holger
PY - 2017/12/14
Y1 - 2017/12/14
N2 - The iron-catalyzed directed ortho-functionalization of arenes developed to an important method in the field of C-H activation. On the other hand, the iron-catalyzed ortho-functionalization of ferrocenes bearing ortho-directing groups (ODGs) has scarcely been investigated. Herein we present the iron-catalyzed ortho-alkylation and -arylation of ODG-substituted ferrocenes bearing a bidentate ODG with the formation of racemic 1,2-disubstituted ferrocenes in up to 94% yield. The approach toward an enantioselective iron-catalyzed C-H activation resulted in an ortho-phenylation with a promising enantiomeric excess of 46%. The first iron-catalyzed diastereoselective ortho-methylation gave an excellent diastereomeric excess of ≥99%.
AB - The iron-catalyzed directed ortho-functionalization of arenes developed to an important method in the field of C-H activation. On the other hand, the iron-catalyzed ortho-functionalization of ferrocenes bearing ortho-directing groups (ODGs) has scarcely been investigated. Herein we present the iron-catalyzed ortho-alkylation and -arylation of ODG-substituted ferrocenes bearing a bidentate ODG with the formation of racemic 1,2-disubstituted ferrocenes in up to 94% yield. The approach toward an enantioselective iron-catalyzed C-H activation resulted in an ortho-phenylation with a promising enantiomeric excess of 46%. The first iron-catalyzed diastereoselective ortho-methylation gave an excellent diastereomeric excess of ≥99%.
UR - http://www.scopus.com/inward/record.url?scp=85041238526&partnerID=8YFLogxK
U2 - 10.1021/acs.organomet.7b00799
DO - 10.1021/acs.organomet.7b00799
M3 - Article
AN - SCOPUS:85041238526
VL - 36
SP - 4979
EP - 4989
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 24
ER -