Photoredox radical benzylation process
AssigneesCentre National De La Recherche Scientifique, Universite De Strasbourg, Universite De Haute Alsace
InventorsElisabeth DAVIOUD-CHARVET, Maxime DONZEL, Mourad ELHABIRI
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Abstract
The present invention relates to a method for the preparation of a compound having the formula (I): wherein: R1, R2, R3, and R4 are in particular H or halogen, R5 is in particular (C1-C6)alkyl, R6 is a group of formula —CH═CH2 or a group having the below formula (II): said method comprising a reacting step carried out under light irradiation in the presence of an iron catalyst, a heteroatomic base, and a HAT agent.
Claims20
A method for preparing a compound of formula (I):
- wherein:
- R1, R2, R3, and R4 are independently from each other selected from the group consisting of:
- H,
- halogen,
- OH,
- (C1-C6)alkyl,
- —O(P═O)OAlk2, Alk being a (C1-C6)alkyl group,
- halo(C1-C6)alkyl,
- halo(C1-C6)alkoxy, and
- (C1-C6)alkoxy,
- R5 is selected from the group consisting of:
- (C1-C6)alkyl,
- OH,
- halogen,
- (C6-C10)aryl,
- (C6-C10)aryloxy,
- (C6-C10)aryl(C1-C6)alkyl, and
- —O—C(═O)—(C1-C6)alkyl,
- R6 is a group of formula —CH═CH2 or a group having the below formula (II):
- wherein:
- n is 0 or an integer varying from 1 to 5;
- and
- R, identical or different, is selected from the group consisting of:
- halo(C1-C6)alkyl,
- (C1-C6)alkyl,
- CN,
- NO2,
- halogen,
- —C(═O)—(C1-C6)alkyl,
- halo(C1-C6)alkoxy,
- (C1-C6)alkoxy,
- or two adjacent R groups may form together with the carbon atoms carrying them a (C6-C10)aryl group or a heterocycloalkyl group;
- said method comprising a step of reacting a compound of formula (III):
- wherein R1, R2, R3, R4, and R5 being as defined above in formula (I);
- with a compound having the following formula (IV):
- X—CH2—R6 (IV);
- wherein R6 being as defined above in formula (I), and
- X being a halogen atom;
- said reacting step being carried out under light irradiation in the presence of an iron catalyst, a heteroatomic base, and a HAT agent.
A compound having the formula (V):
- R7 being selected from the group consisting of:
- halogen,
- (C6-C10)aryl,
- (C6-C10)aryloxy, and
- (C6-C10)aryl(C1-C6)alkyl.
Dependencies are inferred from the claim text.