Hydroboration and borylation with cobalt catalysts
View Patent ↗In one aspect, cobalt complexes are described herein. In some embodiments, such cobalt complexes are operable as catalysts for hydroboration and borylation applications.
1. A method of providing a borylated product comprising:
providing a reaction mixture comprising an aliphatic compound or an aromatic compound, a borylation reagent and a cobalt complex having Formula (IV):
wherein X 1 and X 2 are independently selected from Group VIIA of the Periodic Table and R 1 -R 11 are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-aryl and alkyl-heteroaryl, wherein the alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-aryl and alkyl-heteroaryl are optionally substituted with one or more substituents selected from the group consisting of (C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkenyl, alkoxy, halo, hydroxy, C(O)OR 12 , NR 13 R 14 , wherein R 12 -R 14 are independently selected from the group consisting of hydrogen, (C 1 -C 10 )-alkyl and (C 1 -C 10 )-alkenyl;
adding an activator to the reaction mixture to activate the cobalt complex; and
reacting the aliphatic compound or aromatic compound with the borylation reagent in the presence of the activated cobalt complex or a derivative of the activated cobalt complex.
2. The method of claim 1 , wherein the reaction mixture comprises an aromatic compound having a five-membered aromatic ring or a six-membered aromatic ring.
3. The method of claim 1 , wherein the borylation reagent is a boronic acid derivative.
4. The method of claim 1 , wherein the borylation reagent is a diboron compound.
5. The method of claim 1 , wherein the borylation reagent is selected from the group consisting of bis(pinacolato)diboron, bis(hexylene glycolato)diboron, bis(catecholato)diboron and bis(neopentyl glycolato)diboron.
6. The method of claim 1 , wherein X 1 and X 2 and are chloro and R 1 -R 11 are hydrogen.
7. The method of claim 1 , wherein the reaction mixture comprises the aliphatic compound, and the aliphatic compound is saturated.
8. The method of claim 1 , wherein the reaction mixture comprises the aliphatic compound, and the aliphatic compound is unsaturated.
9. The method of claim 1 , wherein the reaction mixture comprises the aromatic compound.
10. The method of claim 9 , wherein the aromatic compound is five-membered.
11. The method of claim 9 , wherein the aromatic compound is six-membered.
12. The method of claim 1 , wherein and R 1 -R 11 are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.
13. The method of claim 1 , wherein and R 1 -R 11 are independently selected from the group consisting of hydrogen, alkyl and aryl.
14. The method of claim 1 , wherein and R 1 -R 11 are independently selected from the group consisting of hydrogen and alkyl.