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A novel chiral dibenzothiophene skeleton diphosphine ligand and its synthesis method

A technology of dibenzothiophene and bisphosphine ligands, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problem of less research on P-O type ligands

Inactive Publication Date: 2017-03-22
HENAN INST OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Among the known types of bisphosphine ligands, chiral bisphosphine P-O ligands derived from dibenzothiophene are relatively less studied

Method used

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  • A novel chiral dibenzothiophene skeleton diphosphine ligand and its synthesis method
  • A novel chiral dibenzothiophene skeleton diphosphine ligand and its synthesis method
  • A novel chiral dibenzothiophene skeleton diphosphine ligand and its synthesis method

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Experimental program
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Embodiment 1

[0029] A novel central chiral dibenzothiophene bisphosphine ligand with the following structure:

[0030]

[0031] The synthetic method comprises the following three steps:

[0032] The first step, under nitrogen protection, add 10g dibenzothiophene (54mmol) successively in reaction flask,

[0033] 300ml of n-hexane, 20mL of tetramethylethylenediamine (TMEDA), dissolved completely under stirring, slowly add 2.5M butyllithium 45mL dropwise at 0-10°C, reflux reaction for 2 hours after dropping, then cool to 0°C and slowly add 5.9 g acetaldehyde, after the dropwise addition, naturally returned to room temperature and stirred for 5 hours, TLC detected that the reaction was completed, and the reaction solution was poured into ice water, stirred, filtered, and dried to obtain 13.5g solid diol intermediate, which was added with 200mL acetone solvent and 23.7g PCC (0.11mol) was subjected to oxidation reaction, stirred at room temperature for 2-3 hours, after the detection reaction...

Embodiment 2

[0038] A novel chiral dibenzothiophene bisphosphine ligand with the following structure:

[0039]

[0040] The synthetic method is divided into the following three steps:

[0041] The first step, under nitrogen protection, add 10g dibenzothiophene (54mmol) successively in reaction flask,

[0042] 300ml of n-hexane, 20mL of tetramethylethylenediamine (TMEDA), dissolved completely under stirring, slowly add 2.5M butyllithium 54mL dropwise at 0-10°C, reflux reaction for 2 hours after dropping, then cool to 0°C and slowly add 14.6 g benzaldehyde, after the dropwise addition, naturally returned to room temperature and stirred for 5 hours, TLC detected that the reaction was completed, and the reaction solution was poured into ice water, stirred, filtered, and dried to obtain 21.5g solid diol intermediate, which was added with 300mL acetone solvent and 23.7g PCC (0.11mol) was subjected to an oxidation reaction, stirred at room temperature for 2 hours, after the detection reaction...

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Abstract

The invention discloses a novel chirality dibenzothiophene framework diphosphine ligand and a synthetizing method thereof, and belongs to the field of organic synthesis. The synthetizing method comprises the following steps: starting with dibenzothiophene, and removing protons and aldehyde through butyl lithium so as to obtain racemic glycol intermediates; then, oxidizing the intermediates to form ketone by using PCC, and then performing chirality reduction with R-Me-CBS / BH3 so as to obtain chirality alcohol; finally, reacting the chirality alcohol with a phosphine reagent Ph2PNEt2 so as to obtain the chirality dibenzothiophene framework diphosphine ligand.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a novel chiral dibenzothiophene skeleton bisphosphine ligand and a synthesis method thereof. Background technique [0002] Homogeneous asymmetric synthesis reactions catalyzed by transition metal complexes have been a very active research field in recent years, especially in asymmetric hydrogenation reactions. As an important structural unit in the complex, the change of the ligand structure is crucial to the catalytic reaction, and the bisphosphine ligand is one of the most representative ones. Since DIOP, BINAP and other bisphosphine ligands were synthesized, novel chiral bisphosphine ligands have been designed and synthesized successively, and successfully applied to asymmetric catalytic reactions. [0003] In order to continuously enrich the chiral ligands, the chiral spatial structure is becoming more and more diverse, and the applicable range of substrates is bec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6553
Inventor 薛峰祝勇李长恭邓月娥崔茂金王九霞
Owner HENAN INST OF SCI & TECH