Ylide-functionalised phosphanes for use in metal complexes and homogeneous catalysis

Patent metadata

Field	Value
Publication number	US-10940470-B2
Application number	US-201816636962-A
Country	US
Kind code	B2
Filing date	Aug 8, 2018
Priority date	Aug 8, 2017
Publication date	Mar 9, 2021
Grant date	Mar 9, 2021

Abstract

The invention relates to ylide-functionalized phosphane ligands, the production of same and use in transition metal compounds, as well as the use of same as catalysts in organic reactions.

First claim

The invention claimed is:

1. Metal complexes having phosphane ligands of formula (I)

wherein On is a phosphonium group —P(R 3 R 4 R 5 ), in which R 3 , R 4 and R 5 are independently selected from the group consisting of C 1-6 alkyl groups, C 4-10 cycloalkyl groups, C 6-10 aryl groups, X is selected from the group consisting of linear, branched-chain or cyclic C 1-6 alkyl groups, C 6-10 aryl groups, mono- or polyunsaturated linear, branched-chain or cyclic C 2-6 alkenyl groups, a trialkylsilyl (—SiR 3 R 4 R 5 ), arylsulfonyl group, and R 1 and R 2 are C 6-10 aryl groups or C 1-6 alkyl and cycloalkyl groups, with the proviso that ligands where R 1 and R 2 are phenyl, On is triphenylphosphine (PPh 3 ) and X is phenyl or methyl are excluded.

2. The metal complexes according to claim 1 , wherein R 3 , R 4 and R 5 are independently selected from the group consisting of methyl, ethyl, butyl, cyclohexyl, phenyl, and combinations thereof.

3. The metal complexes according to claim 1 , wherein X is selected from the group consisting of methyl, ethyl, cyclohexyl, phenyl, p-tolyl, trimethylsilyl, p-tolylsulfonyl, or combinations thereof.

4. The metal complexes according to claim 1 , wherein said complex is a palladium allyl complex having the following structure (V)

wherein X′ is an anion,
Y is On-C—X,
R 33 , R 34 and R 35 are independently selected from H, alkyl, aryl and heteroaryl groups that may be unsubstituted or substituted with functional groups; or at least two of R 33 , R 34 and R 35 form a carbocyclic ring with 5 to 14 carbon atoms, Ar represents a substituted or unsubstituted aryl group.

5. The metal complexes according to claim 4 , wherein R 33 , R 34 and R 35 are independently selected from linear, branched-chain or cyclic C 1-10 alkyl groups, the aryl groups are selected from C 6-14 aryl groups, the alkenyl groups are selected from mono- or polyunsaturated linear, branched-chain or cyclic C 2-10 alkenyl groups, and the heteroaryl groups are selected from C 6-14 heteroaryl groups, wherein all of the groups mentioned are optionally substituted with functional groups; or
at least two of R 33 , R 34 and R 35 form a carbocyclic ring that is a C 4-10 cycloalkyl group, or a C 6-14 aryl group, optionally substituted with one or more functional groups; and
Ar are selected from C 6-14 aryl groups and the heteroaryl groups are selected from C 6-14 heteroaryl groups, wherein all of the groups mentioned are optionally substituted with functional groups; and
the functional groups are selected from C 1-6 alkyl groups, C 6-10 aryl, halogen, hydroxy, cyano, alkoxy, amino, or mercapto.

6. The metal complexes of claim 1 , wherein the metal of the metal complex is selected from the group consisting of copper, silver, gold, platinum, palladium, nickel, and combinations thereof.

7. A process for performing a coupling reaction containing the steps of
providing a reaction mixture containing at least a substrate, coupling partner, and the metal complex according to claim 1 ; and
reacting said substrate with said coupling partner in the presence of the metal complex or its derivative to form a coupling product.

8. The process according to claim 7 , wherein the metal of said metal complex is a precious metal or a transition metal.

9. The process according to claim 7 , wherein the metal of said metal complex is a metal of group 10 or 11 of the Periodic Table of the elements.

10. The process according to claim 7 , wherein the metal of said metal complex is selected from the group consisting of copper, silver, gold, platinum, palladium, nickel, and combinations thereof.

Assignees

• Umicore Ag & Co Kg

Inventors

• Däschlein-Gessner Viktoria
• Scherpf Thorsten

Classifications

• C07F15/04

  Nickel compounds · CPC title

• C07F15/006

  Palladium compounds · CPC title

• C07F9/54 Primary

  Quaternary phosphonium compounds · CPC title

• C07F1/12

  Gold compounds · CPC title

• C07B43/00

  Formation or introduction of functional groups containing nitrogen · CPC title