US 12,351,924 B2
Electroreductive cross coupling
Christo Sevov, Columbus, OH (US); and Taylor Hamby, Columbus, OH (US)
Assigned to Ohio State Innovation Foundation, Columbus, OH (US)
Filed by OHIO STATE INNOVATION FOUNDATION, Columbus, OH (US)
Filed on Feb. 9, 2023, as Appl. No. 18/166,604.
Claims priority of provisional application 63/308,319, filed on Feb. 9, 2022.
Prior Publication US 2023/0250539 A1, Aug. 10, 2023
Int. Cl. C25B 3/05 (2021.01); C25B 3/03 (2021.01); C25B 3/07 (2021.01); C25B 3/09 (2021.01); C25B 3/29 (2021.01)
CPC C25B 3/05 (2021.01) [C25B 3/03 (2021.01); C25B 3/07 (2021.01); C25B 3/09 (2021.01); C25B 3/29 (2021.01)] 20 Claims
OG exemplary drawing
 
1. A process for forming a compound of Formula (I):

OG Complex Work Unit Chemistry
wherein Ra is selected from hydrogen, C1-12alkyl, aryl, C1-12heteroaryl, C3-12cycloalkyl, or C1-12 heterocyclyl;
wherein Rb is selected from hydrogen, C1-12alkyl, aryl, C1-12heteroaryl, C3-12cycloalkyl, or C1-12 heterocyclyl;
wherein Rc is selected from hydrogen, C1-12alkyl, aryl, C1-12heteroaryl, C3-12cycloalkyl, or C1-12 heterocyclyl;
wherein R1 is selected from C1-12alkyl, aryl, C1-12heteroaryl, C3-12cycloalkyl, or C1-12 heterocyclyl;
wherein R2 is selected from C1-12alkyl, aryl, C1-12heteroaryl, C3-12cycloalkyl, or C1-12 heterocyclyl;
wherein R3 is selected from hydrogen, C1-12alkyl, aryl, C1-12heteroaryl, C3-12cycloalkyl, or C1-12 heterocyclyl;
wherein any two or more of Ra, Rb, Rc, R1, R2, and R3 may together form a ring;
comprising electrolyzing a mixture of:
a) an sp2 donor of Formula (a):

OG Complex Work Unit Chemistry
wherein X is F, Cl, Br, I, OSO2R, OC(═O)R, B(OH)2, BF3, BR2, B(OR)2, B(OC(═O)R)2, B(NHR)2, B(OR)3, wherein R is in each case independently selected from C1-8alkyl, aryl, C1-8-cycloalkyl, C1-8heterocyclyl, and C1-8heteroaryl, each R optionally substituted one or more times by F, Cl, Br, I, NO2, and wherein two or more R groups may together form a ring;
b) an sp3 donor of Formula (b):

OG Complex Work Unit Chemistry
wherein Z is F, Cl, Br, I, OSO2R, OC(═O)R, B(OH)2, BF3, BR2, B(OR)2, B(OC(═O)R)2, B(NHR)2, B(OR)3, wherein R is in each case independently selected from C1-8alkyl, aryl, C1-8-cycloalkyl, C1-8heterocyclyl, and C1-8heteroaryl, each R optionally substituted one or more times by F, Cl, Br, I, NO2, and wherein two or more R groups may together form a ring;
c) a catalyst system comprising:
i) a transition metal selected from Ni, Mn, Fe, Cu, Co, or a combination thereof;
ii) a tridentate ligand; and
iii) a tertiary organophosphine.