Monophosphite ligands having a tert-butyloxycarbonyl group

1. A ligand having structure I or II:

wherein

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from the group consisting of: —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, halogen, COO—(C 1 -C 12 )-alkyl, CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 ;

X and Y are each independently selected from the group consisting of

—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-O—(C 1 -C 12 )-alkyl, —(C 1 -C 12 )-alkyl-(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl-COO—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —(C 4 -C 20 )-heteroaryl, —(C 4 -C 20 )-heteroaryl-(C 1 -C 12 )-alkyl, and —(C 5 -C 8 )-cycloalkyl-(C 4 -C 20 )-aryl-CO—(C 6 -C 20 )-aryl,

Z is selected from the group consisting of

—(C 1 -C 12 )-alkyl-, —(C 6 -C 20 )-aryl-, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl-, —(C 1 -C 12 )-alkyl-(C 6 -C 20 )-aryl-, —(C 4 -C 20 )-heteroaryl-, —(C 6 -C 20 )-aryl-CO—(C 6 -C 20 )-aryl-, and —(C 6 -C 20 )-aryl-(C 6 -C 20 )-aryl-;

wherein the alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups mentioned are optionally substituted.

2. The ligand according to claim 1 , wherein X and Y are each independently selected from the group consisting of

—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-O—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-COO—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —(C 4 -C 20 )-heteroaryl, and —(C 4 -C 20 )-heteroaryl-(C 1 -C 12 )-alkyl.

3. The ligand according to claim 1 , wherein X and Y are each independently selected from the group consisting of

—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-O—(C 1 -C 12 )-alkyl, and —(C 6 -C 20 )-aryl-COO—(C 1 -C 12 )-alkyl.

4. The ligand according to claim 1 , wherein Z is selected from the group consisting of

—(C 1 -C 12 )-alkyl-, —(C 6 -C 20 )-aryl-, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl-, —(C 6 -C 20 )-aryl-CO—(C 6 -C 20 )-aryl-, —(C 1 -C 12 )-alkyl-(C 6 -C 20 )-aryl-, and —(C 6 -C 20 )-aryl-(C 6 -C 20 )-aryl-.

5. The ligand according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from the group consisting of —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, —COO—(C 1 -C 12 )-alkyl, —CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 .

6. The ligand according to claim 1 , wherein X and Y are the same radicals.

7. The ligand according to claim 1 , wherein R 3 and R 6 are each —O—(C 1 -C 12 )-alkyl.

8. The ligand according to claim 1 , wherein R 3 and R 6 are each —OMe.

9. The ligand according to claim 1 , wherein R 1 and R 8 are each —(C 1 -C 12 )-alkyl.

10. The ligand according to claim 1 , wherein R and R 8 are each tert-butyl.

11. The ligand according to claim 1 , having the general structure III:

wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 are each independently selected from the group consisting of

—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, -halogen, —COO—(C 1 -C 12 )-alkyl, —CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 .

12. The ligand according to claim 1 , having the general structure IV:

wherein R 9 , R 10 , R 1 , R 12 , R 13 , R 14 , R 15 , R 16 are each independently selected from the group consisting of

—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, -halogen, —COO—(C 1 -C 12 )-alkyl, —CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 .

13. The ligand according to claim 1 , which has the structure I.

14. The ligand according to claim 1 , which has the structure II.

15. The ligand according to claim 1 , which has a structure selected from the group consisting of the following structures 1 to 70:

16. A complex, comprising:

the ligand according to claim 1 , and

a metal atom selected from the group consisting of Rh, Ru, Co, and Ir.

17. A process for the hydroformylation of an olefin, comprising:

a) initially charging an olefin,

b) adding

the complex according to claim 13 , to obtain a reaction mixture,

c) feeding H 2 and CO into the reaction mixture,

d) heating the reaction mixture, to obtain conversion of the olefin to an aldehyde.

18. A process for the hydroformylation of an olefin, comprising:

a) initially charging an olefin,

b) adding a ligand according to claim 1 and a compound including a metal atom selected from the group consisting of Rh, Ru, Co, and Ir, to obtain a reaction mixture,

c) feeding H 2 and CO into the reaction mixture,

d) heating the reaction mixture, to obtain conversion of the olefin to an aldehyde.