IP Library Granted Patent US 12,240,866
Granted Patent B2
US 12,240,866 · App. 17/753,700 · Granted Mar 4, 2025

Transition metal dimer complex as a catalyst

Inventors: Rachel Kahan (Cambridge, GB); Mateusz Pitak (Cambridge, GB); Carin Seechurn (Cambridge, GB)
Assignee: Johnson Matthey Public Limited Company
C07F17/02B01J31/2404C07F15/0066
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Quick Facts
Patent No.
US 12,240,866
App. No.
17/753,700
Granted
Mar 4, 2025
Kind
B2
Abstract

A compound of formula (I) wherein M is Pd(II) or Ni(II); X is a halide; R 1 and R 2 are independently organic groups having 1-20 carbon atoms, or R 1 and R 2 are linked to form a ring structure with the phosphorus atom; R 3 is an organic group having 1-20 carbon atoms; provided that R 1 , R 2 , R 3 are not each phenyl.

Claims (33)

1. A compound of formula (I)

wherein M is Pd(II) or Ni(II);

X is a halide;

R 1 and R 2 are independently organic groups having 1-20 carbon atoms, or R 1 and R 2 are linked to form a ring structure with the phosphorus atom;

R 3 is an organic group having 1-20 carbon atoms;

provided that R 1 , R 2 , R 3 are not each phenyl.

2. The compound according to claim 1 , wherein M is Pd.

3. The compound according to claim 1 , wherein X is Cl, Br or I.

4. The compound according to claim 1 , wherein X is Cl or Br.

5. The compound according to claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl wherein the heteroatoms are independently selected from sulphur, nitrogen and oxygen.

6. The compound according to claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of alkyl, cycloalkyl and aryl.

7. The compound according to claim 1 , wherein R 3 is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl and metallocenyl.

8. The compound according to claim 1 , wherein PR 1 R 2 R 3 is selected from the group:

Ad=adamantyl

Cy=cyclohexyl

Bn=benzyl

Ar=2,6 dimethoxyphenyl

Mes=2,4,6-trimethylphenyl.

9. A process for the preparation of a compound of formula (IA)

[M 2 Cl 6 ][HPR 1 R 2 R 3 ] 2   (IA)

wherein M is Pd(II) or Ni(II);

R 1 and R 2 are independently organic groups having 1-20 carbon atoms, or R 1 and R 2 are linked to form a ring structure with the phosphorus atom;

and R 3 is an organic group having 1-20 carbon atoms

provided that R 1 , R 2 , and R 3 are not each phenyl,

said process comprising the step of reacting a compound of formula H 2 PdCl 4 with ligand PR 1 R 2 R 3 or a salt thereof.

10. A process for the preparation of a compound of formula (IB)

[M 2 X′ 6 ][HPR 1 R 2 R 3 ] 2   (IB)

wherein M is Pd(II) or Ni(II);

R 1 and R 2 are independently organic groups having 1-20 carbon atoms, or R 1 and R 2 are linked to form a ring structure with the phosphorus atom;

R 3 is an organic group having 1-20 carbon atoms provided that R 1 , R 2 , and R 3 are not each phenyl;

and X′ is bromide, iodide or fluoride, said process comprising the step of reacting a compound of formula H 2 PdCl 4 with ligand PR 1 R 2 R 3 or a salt thereof and a compound ZX′ wherein Z is hydrogen or a monovalent metal ion.

11. A process for carrying out a carbon-carbon coupling reaction comprising a step of contacting a compound according to claim 1 as a catalyst to a mixture of reactants.

12. A process for carrying out a carbon-heteroatom coupling reaction comprising a step of contacting a compound according to claim 1 as a catalyst to a mixture of reactants.

Assignments (2)
CHANGE OF ADDRESS Recorded Jan 14, 2026
From: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
To: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
Reel/Frame 074703/0733 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2022
From: KAHAN, RACHEL; PITAK, MATEUSZ; SEECHURN, CARIN
To: JOHNSON MATTHEY PUBLIC LIMITED
Reel/Frame 059646/0892 →
Priority Claims (1)
GB 1918871 · Dec 19, 2019 · national
Continuity (1)
Related Publication 20220356200A1 · Nov 10, 2022
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