Dihydroguaiazulenide Complexes and Catalysts of Group 8–12 Transition Metals: Ligands from Renewable Feedstock Replace, even Outmatch Petrochemical Based Cyclopentadienyl Chemistry DOI Creative Commons
Tobias Vollgraff, Angelino Doppiu, Jörg Sundermeyer

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(7)

Published: Nov. 13, 2023

We present an in-depth study of the sterically demanding Cp-synthon (8-H-GuaH)Li isolated from natural product guaiazulene (Gua) as a ligand transfer reagent towards late transition metal complex precursors. The synthesis and full characterization selected, essentially unexplored homo- heteroleptic 8-H-guaiazulenide complexes iron, ruthenium, cobalt, rhodium, platinum, copper zinc are discussed in detail. In order to demonstrate their potential catalytic applications, [(GuaH)PtMe

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

Application of Planar Chiral Cyclopentadienyl Rhodium Catalysts without Chiral Substituents in Asymmetric C—H Activation DOI
Yu Zou,

Weicong Guo,

Jun Wang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 466 - 466

Published: Jan. 1, 2025

Language: Английский

Citations

0

Planar Chiral Rhodium Complex Based on the Tetrahydrofluorenyl Core for Enantioselective Catalysis DOI
Vladimir B. Kharitonov, Evgeniya Podyacheva, Denis Chusov

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(49), P. 8906 - 8911

Published: Dec. 5, 2023

A simple four-step route to a chiral tetrahydrofluorenyl rhodium catalyst from naturally occurring (−)-α-pinene was developed. Our approach does not use multistep and time-consuming procedures such as HPLC or diastereomeric resolution. The key success lies in the face-selective coordination of sterically hindered ligand, giving only one complex. This proved be highly efficient for asymmetric C–H annulation aryl hydroxamates with alkenes (yield up 95%, 91% ee) at low loading (up 0.4 mol % based on Rh).

Language: Английский

Citations

10

[2.2]Benzoindenophane‐Based Chiral Indenyl Ligands: Design, Synthesis, and Applications in Asymmetric C−H Activation DOI

Weicong Guo,

Ji‐Jun Jiang, Jun Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(32)

Published: May 23, 2024

Abstract Development of chiral indenyl ligands for asymmetric C−H activation is a longstanding challenge, and extremely few successes have been achieved. In this paper, we describe class readily accessible, facilely tunable user‐friendly featuring [2.2]benzoindenophane skeleton via divergent synthesis strategy. The corresponding rhodium catalysts were successfully applied in the reaction O‐Boc hydroxybenzamide with alkenes to give various dihydroisoquinolone products (up 97 % yield, up 98 ee). Moreover, carboxylic acids alkynes was also accomplished, providing range axially isocoumarins 99 94 Notably, represents first example enantioselective transition metal catalyzed C(sp 2 )−H activation/oxidative coupling benzoic internal construct isocoumarins. Given many attractive features ligands, such as convenient synthesis, high tunability exclusive face‐selectivity coordination, its applications more catalytic other catalysis are foreseen.

Language: Английский

Citations

3

Enantioselective Synthesis of Indole‐Derivated Axially Chiral Frameworks via CpXRh(III)‐Catalyzed Domino Cyclization/C3‐Arylation of 2‐Alkynylanilines with 1‐Diazonaphthoquinones DOI
Junwei Ye,

Qingwei Song,

Dongping Pan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1064 - 1069

Published: Jan. 13, 2024

Abstract We report herein a chiral Cp X Rh(III)‐catalyzed domino cyclization/C 3 ‐arylation process using 2‐alkynylanilines and 1‐diazonaphthoquinones as viable substrates, delivering indole‐based derivatives endowed with axial chirality. The method features high enantioselectivity, broad substrate scope, robust functional group tolerance. Subsequent functionalization of the synthesized scaffolds underlines practicality this approach in design indole‐derivated axially frameworks, demonstrating its substantial promise synthetic medicinal chemistry applications.

Language: Английский

Citations

1

Precise Construction of Chiral Plasmonic Nanoparticles for Enantioselective Discrimination DOI

Lingyan Kan,

Zhenqian Zhang, Junle Zhang

et al.

The Journal of Physical Chemistry Letters, Journal Year: 2024, Volume and Issue: 15(30), P. 7740 - 7747

Published: July 24, 2024

Chiral plasmonic nanostructures exhibit potential in the advanced manufacturing industry, due to their fascinating characteristics. However, limitation of existing fabrication methods as difficulty precisely manipulate chiral at nanoscale restricts application and optimization performance. In this work, we report a simple robust route for precise construction Au nanoparticles (NPs), employing star-like block copolymers with well-defined structures templates. The globular unimolecular micelles nanoreactors enabled control over size, shape, chirality situ grown nanocrystals. Utilizing anisotropy property surface-enhanced Raman scattering (SERS), enantioselective discrimination on various substrates was accomplished an enhancement factor 9.3 × 106. NPs smaller size exhibited strengthened recognition. Furthermore, these unimolecular-micelle-based templates high efficiency strong controllability could pave way tailor-made nanomaterials.

Language: Английский

Citations

1

Chiral Bis(binaphthyl) Cyclopentadienyl Ligands for Rhodium-Catalyzed Desymmetrization of Diarylmethanes via Selective Arene Coordination DOI

Wen‐Qiang Wu,

Pei‐Pei Xie, Leyao Wang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

Owing to substantial advances in the past several decades, transition-metal-catalyzed asymmetric reactions have garnered considerable attention as pivotal methods for constructing chiral molecules from abundant, readily available achiral counterparts. These are largely attributed development of ligands that control stereochemistry through steric repulsion and other noncovalent interactions between functional groups or prochiral centers on substrates. However, stereocontrol weakens dramatically with increasing distance reaction site group center. Herein, we report a symphonic strategy remote Rh(III)-catalyzed benzylic C-H bond addition diarylmethanes which two aryl motifs differ at

Language: Английский

Citations

1

Enantiospecific Synthesis of Planar Chiral Rhodium and Iridium Cyclopentadienyl Complexes: Enabling Streamlined and Computer-Guided Access to Highly Selective Catalysts for Asymmetric C–H Functionalizations DOI Creative Commons
Sebastian Young Ye, Aragorn Laverny, Matthew D. Wodrich

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

Chiral cyclopentadienyl (Cp

Language: Английский

Citations

1

Rhodium complexes with planar-chiral cyclopentadienyl ligands: synthesis from tert-butylacetylene and catalytic performance in C-H activation of arylhydroxamates DOI
Andrey V. Kolos, Yulia V. Nelyubina, Evgeniya Podyacheva

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(45), P. 17005 - 17010

Published: Jan. 1, 2023

Rhodium complexes with various planar-chiral cyclopentadienyl ligands were synthesized in 1–3 steps by the unusual 2 + 1-cyclotrimerization of tert -butylacetylene.

Language: Английский

Citations

2

[2.2]Benzoindenophane‐Based Chiral Indenyl Ligands: Design, Synthesis, and Applications in Asymmetric C−H Activation DOI

Weicong Guo,

Ji‐Jun Jiang, Jun Wang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(32)

Published: May 23, 2024

Abstract Development of chiral indenyl ligands for asymmetric C−H activation is a longstanding challenge, and extremely few successes have been achieved. In this paper, we describe class readily accessible, facilely tunable user‐friendly featuring [2.2]benzoindenophane skeleton via divergent synthesis strategy. The corresponding rhodium catalysts were successfully applied in the reaction O‐Boc hydroxybenzamide with alkenes to give various dihydroisoquinolone products (up 97 % yield, up 98 ee). Moreover, carboxylic acids alkynes was also accomplished, providing range axially isocoumarins 99 94 Notably, represents first example enantioselective transition metal catalyzed C(sp 2 )−H activation/oxidative coupling benzoic internal construct isocoumarins. Given many attractive features ligands, such as convenient synthesis, high tunability exclusive face‐selectivity coordination, its applications more catalytic other catalysis are foreseen.

Language: Английский

Citations

0