The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Aug. 31, 2021

Filed:

May. 06, 2019
Applicant:

Colorado State University Research Foundation, Fort Collins, CO (US);

Inventors:

Garret Miyake, Fort Collins, CO (US);

Chern-Hooi Lim, Fort Collins, CO (US);

Max Kudisch, Fort Collins, CO (US);

Bin Liu, Fort Collins, CO (US);

Assignee:
Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07D 295/073 (2006.01); C07D 211/62 (2006.01); C07D 211/46 (2006.01); C07C 209/68 (2006.01); C07D 307/52 (2006.01); C07D 213/74 (2006.01); C07D 213/38 (2006.01); C07D 239/26 (2006.01); C07D 235/26 (2006.01); B01J 19/12 (2006.01); B01J 27/08 (2006.01); B01J 35/00 (2006.01); C07D 211/06 (2006.01);
U.S. Cl.
CPC ...
C07D 295/073 (2013.01); B01J 19/123 (2013.01); B01J 27/08 (2013.01); B01J 35/004 (2013.01); C07C 209/68 (2013.01); C07D 211/06 (2013.01); C07D 211/46 (2013.01); C07D 211/62 (2013.01); C07D 213/38 (2013.01); C07D 213/74 (2013.01); C07D 235/26 (2013.01); C07D 239/26 (2013.01); C07D 307/52 (2013.01); B01J 2219/0877 (2013.01); B01J 2219/0892 (2013.01); B01J 2219/1203 (2013.01); C07C 2601/14 (2017.05);
Abstract

The disclosure relates to a method for forming aryl carbon-nitrogen bonds and to photoreactors useful in these and other light-driven reactions. The method comprises contacting an aryl halide, such as 4-bromobenzotrifluoride, with an amine, such as morpholine, in the presence of a Ni salt catalyst solution and an optional base, thereby forming a reaction mixture; exposing the reaction mixture to light under reaction condition sufficient to produce the aryl carbon-nitrogen bonds, e.g., to give a product such as 4-(4-(trifluoromethyl)phenyl)morpholine. In certain embodiments, the amine may be present in a molar excess to the aryl halide. In certain embodiments, the Ni salt catalyst solution includes a Ni(II) salt and a polar solvent, wherein the Ni(II) salt is dissolved in the polar solvent. In certain embodiments, the reactions conditions include holding the reaction mixture at between about room temperature and about 80° C. for between about 1 hour and about 20 hours such that at least about 50% yield is obtained.


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