Title: Photocatalyst-free, light-induced carbon-sulfur cross-coupling methods

Abstract

In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.

Inventors:

Miyake, Garret; Liu, Bin; Lim, Chern-Hooi

Issue Date:

2022-08-30

Research Org.:

Univ. of Colorado, Denver, CO (United States)

Sponsoring Org.:

USDOE Advanced Research Projects Agency - Energy (ARPA-E)

OSTI Identifier:

1925030

Patent Number(s):

11427536

Application Number:

16/019,914

Assignee:

The Regents of the University of Colorado, A Body Corporate (Denver, CO)

Patent Classifications (CPCs):

B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

B01J19/123 - {Ultra-violet light}
B01J19/127 - {Sunlight

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C2603/24 - Anthracenes
C07C2603/50 - Pyrenes
C07C319/14 - of sulfides
C07C321/30 - Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings
C07C323/09 - having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
C07C323/20 - with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
C07C323/21 - with the sulfur atom of the thio group bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
C07C323/22 - containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
C07C323/37 - the sulfur atom of the sulfide group being further bound to a carbon atom of a six-membered aromatic ring
C07C323/62 - having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

C07D213/70 - Sulfur atoms
C07D215/36 - Sulfur atoms
C07D235/28 - Sulfur atoms
C07D239/38 - One sulfur atom
C07D277/74 - Sulfur atoms substituted by carbon atoms
C07D285/16 - Thiadiazines
C07D285/22 - condensed with one six-membered ring
C07D311/54 - substituted in the carbocyclic ring

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DOE Contract Number:  

AR0000683

Resource Type:

Patent

Resource Relation:

Patent File Date: 06/27/2018

Country of Publication:

United States

Language:

English