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 -