Unlock instant, AI-driven research and patent intelligence for your innovation.

Remote heteroaryl alkenylation with catalytic bifunctional template

A heteroaryl and template technology, applied in organic chemistry, chemical recycling, platinum-based organic compounds, etc., can solve problems such as lack of reactivity, remote meta-selective C-H activation has not been successful, etc.

Active Publication Date: 2019-12-06
THE SCRIPPS RES INST
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To date, the use of hydrogen-bonding approaches to achieve Pd-catalyzed long-range meta-selective C–H activation has not been successful due to lack of reactivity.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Remote heteroaryl alkenylation with catalytic bifunctional template
  • Remote heteroaryl alkenylation with catalytic bifunctional template
  • Remote heteroaryl alkenylation with catalytic bifunctional template

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0072] 1. General information

[0073] All reagents were purchased from commercial suppliers and used without further purification unless otherwise stated. Anhydrous solvents were obtained from a solvent purification system manufactured by JC Meyer Solvent Systems. Analytical thin layer chromatography (TLC) was performed on Merck Millipore precoated (0.25 mm thick) silica gel plates with F254 indicator. Visualization is by UV irradiation at 254nm or PMA or KMnO 4 staining solution. Flash column chromatography was performed on silica gel (32-63 μm) supplied by Dynamic Adsorbents. 1 H NMR spectra were recorded on a Bruker DRX-600 spectrometer (600 MHz) in a deuterated solvent, and chemical shifts are reported in ppm (δ) relative to tetramethylsilane used as an internal standard (where the solvent resonates) (CDCl 3 , δ7.26ppm; DMSO-d 6 , δ2.50ppm; acetonitrile-d 3 , δ1.94ppm). Data are reported as follows: chemical shift, multiplicity (s = singlet, d = doublet, t = triple...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

We report the design of a catalytic, bifunctional template that binds heterocyclic substrate via reversible coordination instead of covalent linkage, allowing remote site- selective C-H olefination ofheterocycles. The two metal centers coordinated to this template play different roles; anchoring substrates to the proximity of catalyst and cleaving the remote C-H bonds respectively. Using this strategy, we demonstrate remote site-selective C-H olefination of heterocyclic substrates which do not have functional group handles for covalently attaching templates. For instance the olefination can be an alkenylation of a 3-phenylpyridine with an acrylate alkyl ester selective for the meta position of the phenyl group with respect to the pyridine, or can be an alkenylation of a quinoline with anacrylate alkyl ester selective for the 5-position of the quinoline.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application Serial No. 62 / 458,750, filed February 14, 2017, the entire contents of which are incorporated herein by reference. [0003] Statement of Government Support [0004] This invention was made with government support under 1R01 GM102265 awarded by the National Institutes of Health. The government has certain rights in this invention. Background technique [0005] Direct conversion of C–H bonds to carbon–carbon and carbon–heteroatom bonds can significantly improve step economy in synthesis by providing alternative breaks for traditional functional group manipulations. In this case, for regioselective functionalization 1-5 Directional C–H activation reactions have been extensively studied. Although distance from the directing group and molecular shape can severely limit applicability, a number of methods have been developed to overcome this limitation 6-12 . ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/44A61K31/4406
CPCC07D213/71C07D213/81C07F15/0066Y02P20/582C07D213/04C07D215/06C07F15/0093
Inventor 于金泉
Owner THE SCRIPPS RES INST