Photocatalysts, preparation and use thereof
AssigneeThe Royal Institution for the Advancement of Learning/Mcgill University
InventorsChao-Jun LI, Jianbin LI, Chia-Yu HUANG
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Abstract
There is provided a process for alkylating a substrate with a photocatalytic system. The process comprises providing a mixture containing an acid, and a substrate (an organic compound). Then, an organophotoredox catalyst of formula Ia is contact with the mixture. Finally, the organophotoredox catalyst is activated with a light irradiation to alkylate the substrate and form a carbon covalent bond.
Claims25
A process for alkylating a substrate with a photocatalytic system, the process comprising:
- a) providing mixture comprising an acid, and the substrate, the substrate being an organic compound;
- b) contacting an organophotoredox catalyst of formula Ia with the mixture of step a)
- wherein R1, R1′, R1″ are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted X-alkyl, chemical linker, or X-chemical linker with X being one of an oxygen, an amine or a sulfur, X1, and X2 are independently selected from CH or N, when X1 is N, X2 is CH, R1 and R1′ are hydrogen, when X2 is N, X1 is CH, R1 and R1″ are hydrogen, when X1, and X2 are both CH, R1′ and R1″ are hydrogen,
- wherein R2, R2′, R2″ are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted X-alkyl, chemical linker, or X-chemical linker with X being one of an oxygen,
- an amine or a sulfur, X3, and X4 are independently selected from CH or N, when X3 is N, X4 is CH, R2 and R2″ are hydrogen, when X4 is N, X3 is CH, R2 and R2′ are hydrogen, when X3, and X4 are both CH, R2′ and R2″ are hydrogen,
- wherein R1, R1′, R1″, R2, R2′, R2″ are not all hydrogen,
- wherein R3, R4, R5, and R6 are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl;
- and
- c) activating the organophotoredox catalyst of step b) with a light irradiation to alkylate the substrate and form a carbon covalent bond.
The process according to claim , wherein the alkylation precursor is an alkyltrifluoroborate salt,
- Boc2(NH)—SO2-alkyl, NH3COO-alkyl,
The process according to claim , wherein the alkylation precursor comprises an alkyl moiety functionalized with one or more of an ester, a ketone, an ethereal, a carbamoyl, a benzyloxy, an allyloxy, and propargyloxy.
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A compound of formula Ia
- wherein R1, R1′, R1″ are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted X-alkyl, chemical linker, or X-chemical linker with X being one of an oxygen, an amine or a sulfur, X1, and X2 are independently selected from CH or N, when X1 is N, X2 is CH, R1 and R1′ are hydrogen, when X2 is N, X1 is CH, R1 and R1″ are hydrogen, when X1, and X2 are both CH, R1′ and R1″ are hydrogen,
- wherein R2, R2′, R2″ are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted X-alkyl, chemical linker, or X-chemical linker with X being one of an oxygen, an amine or a sulfur, X3, and X4 are independently selected from CH or N, when X3 is N, X4 is CH, R2 and R2″ are hydrogen, when X4 is N, X3 is CH, R2 and R2′ are hydrogen, when X3, and X4 are both CH, R2′ and R2″ are hydrogen,
- wherein R1, R1′, R1″, R2, R2′, R2″ are not all hydrogen,
- wherein at least one of X1, X2 X3, and X4 is N,
- and wherein R3, R4, R5, and R6 are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl.
A compound selected from the group consisting of
Dependencies are inferred from the claim text.