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Spiro-framework-based cyclopentadiene compounds, rhodium complexes, and synthesis method and application thereof

A technology of cyclopentadiene and rhodium complexes, applied in the direction of organic compound/hydride/coordination complex catalysts, rhodium organic compounds, platinum group organic compounds, etc., can solve the problem of poor enantioselectivity control and skeleton Scarcity and other issues, to achieve high enantioselectivity and high efficiency

Active Publication Date: 2016-06-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, the skeletons of this kind of chiral C2-symmetric cyclopentadiene ligands are relatively rare, and the enantioselectivity control of some reactions is still not good.

Method used

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  • Spiro-framework-based cyclopentadiene compounds, rhodium complexes, and synthesis method and application thereof
  • Spiro-framework-based cyclopentadiene compounds, rhodium complexes, and synthesis method and application thereof
  • Spiro-framework-based cyclopentadiene compounds, rhodium complexes, and synthesis method and application thereof

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Experimental program
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Embodiment 1

[0099] Embodiment 1: Synthesis based on helical chiral cyclopentadiene compound (S)-K1:

[0100]

[0101] Synthesis of (S)-VI-1: Under argon protection, in a 100mL sealed tube, add (S)-VII (0.92g, 3mmol), Pd(OAc) 2 (134.7mg, 0.6mmol), iodobenzene acetate (2.42g, 7.5mmol), iodine (1.9g, 7.5mmol) and DMF (30mL), stirred and dissolved, heated to 100°C, and stirred for 36 hours. The reaction was cooled to room temperature, the solvent was removed under reduced pressure, and saturated Na 2 SO 3 (30 mL), then acidified to acidic with 1N HCl (30 mL), extracted anhydrous Na with DCM 2 SO 4 dry. After filtration, the solvent was distilled off under reduced pressure, and the crude product was separated by column chromatography (petroleum ether / ethyl acetate / acetic acid: 4 / 1 / 0.01).

[0102]

[0103] White solid, 70% yield, m.p.>300℃. 1 HNMR (400MHz, DMSO-d 6 )δ8.19(d, J=8.0Hz, 2H), 7.56(d, J=8.0Hz, 2H), 3.48-3.35(m, 4H), 2.95-2.87(m, 2H), 2.80-2.69(m ,2H); 13 CNMR (100MHz,...

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Abstract

The invention relates to spiro-chiral-framework-based cyclopentadiene rhodium complexes, and a synthesis method and application thereof. The cyclopentadiene rhodium complexes have the optically pure compounds of which the structural formula is disclosed in the specification. The method provided by the invention can be used for synthesizing the rhodium complexes at high yield, and has excellent effects on axially chiral biaryl compound establishment reaction by asymmetric C-H bond oxidation Heck coupling reaction when being used as a catalyst. Particularly, the rhodium complexes usually have excellent enantioselectivity for olefin substrates. Therefore, the complexes have very important meanings for metal-rhodium-catalyzed asymmetric C-H bond functionalization reaction.

Description

technical field [0001] The present invention relates to cyclopentadiene compound based on helical chiral skeleton and its rhodium complex, synthesis method and application, the method can effectively synthesize this cyclopentadiene ligand, and successfully apply the ligand to Preparation of a series of metal rhodium complexes. In the asymmetric oxidative Heck coupling reaction catalyzed by such metal rhodium complexes, a series of axial chiral compounds were constructed with high enantioselectivity. Background technique [0002] The C-H bond functionalization reaction catalyzed by the pentamethylcyclopentadiene rhodium complex can efficiently construct carbon-carbon bonds and carbon-heterobonds, and has been widely used in synthesis. However, until the last few years, there have been no major breakthroughs in the functionalization of asymmetric C–H bonds catalyzed by such rhodium complexes. The Ward and Rovis groups successfully synthesized biotinylated [Cp*Rh(III)] comple...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07C13/72C07C43/21B01J31/22C07D221/10C07D217/02
CPCB01J31/1625B01J31/2295B01J2231/4261B01J2531/0225B01J2531/822C07C13/72C07C43/21C07D217/02C07D221/10C07F15/0073
Inventor 游书力郑军崔文俊
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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