Enantioselective Rh(I)-Catalyzed C–H Arylation of Ferroceneformaldehydes DOI Creative Commons
Chen‐Xu Liu,

Fangnuo Zhao,

Qing Gu

et al.

ACS Central Science, Journal Year: 2023, Volume and Issue: 9(11), P. 2036 - 2043

Published: Sept. 28, 2023

As an important class of platform molecules, planar chiral ferrocene carbonyl compounds could be transformed into various functional groups offering facile synthesis ligands and catalysts. However, developing efficient straightforward methods for accessing enantiopure compounds, especially ferroceneformaldehydes, remains highly challenging. Herein, we report a rhodium(I)/phosphoramidite-catalyzed enantioselective C–H bond arylation ferroceneformaldehydes. Readily available aryl halides such as iodides, bromides, even chlorides are suitable coupling partners in this transformation, leading to series ferroceneformaldehydes good yields excellent enantioselectivity (up 83% yield >99% ee). The aldehyde group diverse smoothly, Ugi's amine PPFA analogues synthesized efficiently. latter was found ligand Pd-catalyzed asymmetric allylic alkylation reactions. Mechanistic experiments supported the formation imine intermediates key step during reaction.

Language: Английский

Planar-chiral arene ruthenium complexes: synthesis, separation of enantiomers, and application for catalytic C–H activation DOI
Mikhail A. Boym, Roman A. Pototskiy, Evgeniya Podyacheva

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(33), P. 4491 - 4494

Published: Jan. 1, 2024

The enantiomers of an arene ruthenium complex were separated by chromatography using auxiliary chiral phosphine. resolved planar-chiral catalyzed asymmetric C–H activation N -methoxy-benzamides.

Language: Английский

Citations

5
H8‐BINOL‐Derived Chiral η6‐Benzene Ligands: New Opportunities for the Ruthenium‐Catalyzed Asymmetric C−H Activation DOI

Junxuan Li,

Guodong Wang,

Weicong Guo

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(31)

Published: April 29, 2024

Abstract Given the tremendous success of (p‐cymene)Ru II ‐catalyzed C−H activation over past 20 years, community has long been aware that development chiral η 6 ‐benzene (Ben) ligands should be a potent strategy for achieving attractive but incredibly underdeveloped ruthenium(II)‐catalyzed asymmetric activation. However, it rarely achieved due to severe difficulty in developing proper Ben ligands. In particular, designing by connecting benzene fragment framework including rings remained an unsolved challenge until this effort. Here we present novel class axially derived from readily available ( S )‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol (( )‐H 8 ‐BINOL) 4–8 steps. Notably, when coordinated with ruthenium, such ligand containing three only forms one possible isomeric BenRu complexes. The related catalysts could effectively catalyze N‐sulfonyl ketimines alkynes, affording range spirocyclic sultams up 99 % yield >99 ee. These are expected find broad applications future.

Language: Английский

Citations

5
Divergent synthesis of pyrrolizine derivatives through C−H bond functionalization of pyrroles DOI

Manqing Wang,

Yuanshuang Xu,

Huihang Hou

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6536 - 6539

Published: Jan. 1, 2024

Presented herein is the synthesis of diversely functionalized pyrrolizines from reaction

Language: Английский

Citations

5
Catalytic Asymmetric C–H Activation/Cyclization of Sulfoximines with Sulfoxonium Ylides by a Chiral η6-Benzene Ruthenium(II) Catalyst DOI
Huan Liu, Ji‐Jun Jiang, Jun Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 17398 - 17404

Published: Nov. 12, 2024

Chiral η6-benzene ruthenium(II) (BenRuII)-catalyzed asymmetric C–H activations are challenging and rarely seen in the literature. Herein, activation/cyclization of sulfoximines with sulfoxonium ylides catalyzed by chiral BenRuII catalyst derived from (S)-H8–BINOL is described. It provides efficient access to various sulfur-chiral 1,2-benzothiazine 1-oxides high yields enantioselectivities (up 99% yield 98% ee). Kinetic resolution racemic was also feasible. The reaction mechanism studied tool H/D exchange kinetic isotope effect. metallacycle revealing origin induction prepared, characterized, proved effective for model reaction. This work demonstrates great potential catalysts activation.

Language: Английский

Citations

5
Enantioselective Rh(I)-Catalyzed C–H Arylation of Ferroceneformaldehydes DOI Creative Commons
Chen‐Xu Liu,

Fangnuo Zhao,

Qing Gu

et al.

ACS Central Science, Journal Year: 2023, Volume and Issue: 9(11), P. 2036 - 2043

Published: Sept. 28, 2023

As an important class of platform molecules, planar chiral ferrocene carbonyl compounds could be transformed into various functional groups offering facile synthesis ligands and catalysts. However, developing efficient straightforward methods for accessing enantiopure compounds, especially ferroceneformaldehydes, remains highly challenging. Herein, we report a rhodium(I)/phosphoramidite-catalyzed enantioselective C–H bond arylation ferroceneformaldehydes. Readily available aryl halides such as iodides, bromides, even chlorides are suitable coupling partners in this transformation, leading to series ferroceneformaldehydes good yields excellent enantioselectivity (up 83% yield >99% ee). The aldehyde group diverse smoothly, Ugi's amine PPFA analogues synthesized efficiently. latter was found ligand Pd-catalyzed asymmetric allylic alkylation reactions. Mechanistic experiments supported the formation imine intermediates key step during reaction.

Language: Английский

Citations

11