IP Library Granted Patent US 10,494,395
Granted Patent B2
US 10,494,395 · App. 15/103,200 · Granted Dec 3, 2019

Base metal catalyzed borylation of arenes and aromatic heterocycles

Inventors: Paul J. Chirik (Princeton, NJ); Scott Semproni (Portland, OR); Jennifer Obligacion (Edison, NJ); Margaret Scheuermann (Plainsboro, NJ)
Assignee: The Trustees of Princeton University
C07F15/065
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Quick Facts
Patent No.
US 10,494,395
App. No.
15/103,200
Granted
Dec 3, 2019
Kind
B2
Abstract

In one aspect, cobalt complexes are described herein. In some embodiments, such cobalt complexes employ bis(phosphine) or bis(imine) ligand and are operable as catalysts for borylation of arenes and aromatic heterocycles.

Claims (20)

1. A cobalt complex is of Formula (IV):

wherein R 1 -R 4 are independently selected from the group consisting of hydrogen and alkyl, and wherein R 5 -R 7 are independently selected from the group consisting of hydrogen, alkyl, and heteroalkyl; and

wherein E 1 and E 2 are independently selected from the group consisting of CR 8 , and C(R 8 ) 2 , wherein R 8 is selected from the group consisting of hydrogen, and alkyl; and

wherein G 1 and G 2 are independently selected from N and P; and

and

and wherein X is R 13 COO—, where R 13 is alkyl.

2. The cobalt complex of Formula (IV), wherein G 1 and G 2 are not each P.

3. The cobalt complex of claim 1 , wherein R 1 -R 4 are independently alkyl.

4. The cobalt complex of claim 3 having the structure:

5. The cobalt complex of claim 3 , having the structure:

6. A cobalt complex is of Formula (IV):

wherein R 1 -R 4 are independently selected from the group consisting of hydrogen and alkyl, and wherein R 5 -R 7 are independently selected from the group consisting of hydrogen, alkyl, and heteroalkyl; and

wherein E 1 and E 2 are independently selected from the group consisting of CR 8 , and C(R 8 ) 2 , wherein R 8 is selected from the group consisting of hydrogen, and alkyl; and

wherein G 1 and G 2 are independently selected from N and P; and

and

and wherein X is R 13 COO—, where R 13 is alkyl and

wherein the cobalt complex of Formula (IV) is operable to participate in borylation of an arene or aromatic heterocycle.

7. The cobalt complex of claim 6 , wherein R 1 -R 4 are independently alkyl.

8. The cobalt complex of claim 7 having the structure:

9. The cobalt complex of claim 7 , having the structure:

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2019
From: CHIRIK, PAUL J.; SEMPRONI, SCOTT; OBLIGACION, JENNIFER; SCHEUERMANN, MARGARET
To: THE TRUSTEES OF PRINCETON UNIVERSITY
Reel/Frame 048483/0198 →
CONFIRMATORY LICENSE Recorded Oct 5, 2016
From: PRINCETON UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 040228/0899 →
Continuity (2)
Provisional Application 61913522 · Dec 9, 2013
Related Publication 20160318963A1 · Nov 3, 2016