US 11,926,911 B2
Microfluidic process for the general electrochemical synthesis of geminal dipseudohalide or halide-pseudohalide compounds
Thorsten G. Schroer, Palmdale, CA (US); Gregory E. LeCroy, Lancaster, CA (US); Miguel Aguila, Palmdale, CA (US); Mayra R. Rodriguez, Lancaster, CA (US); Tyler J. Downard, Phelan, CA (US); and Brianna L. MacLeod, Lancaster, CA (US)
Assigned to United States of America as represented by the Secretary of the Air Force, Wright-Patterson AFB, OH (US)
Filed by Government of the United States, as represented by the Secretary of the Air Force, Wright-Patterson AFB, OH (US)
Filed on Jan. 12, 2023, as Appl. No. 18/153,683.
Claims priority of provisional application 63/267,635, filed on Feb. 7, 2022.
Prior Publication US 2023/0250540 A1, Aug. 10, 2023
Int. Cl. C25B 3/11 (2021.01); C25B 3/26 (2021.01); C25B 3/27 (2021.01); C25B 9/19 (2021.01); C25B 11/091 (2021.01)
CPC C25B 3/11 (2021.01) [C25B 9/19 (2021.01); C25B 11/091 (2021.01)] 14 Claims
OG exemplary drawing
 
1. A process for the microfluidic electrochemical synthesis of geminal dipseudohalide or halide-pseudohalide compounds comprising the steps of:
pumping a solution comprising a compound of Formula I

OG Complex Work Unit Chemistry
wherein for Formula I, R1 and R2 are any combination of H, methyl (—CH3), ethyl (—CH2CH3), propyl (—CH2CH2CH3), hydroxy (—OH), methoxy (—CH2OH), ethoxy (—CH2CH2OH), methyl ester (—CH2COOCH3), propyl methyl ester (—CH2CH2COOCH3), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidine, oxetane, 2,2-dimethyl-1,3,dioxane, and phenyl, and X is a pseudohalide moiety selected from the group consisting of nitro (—NO2), cyano (—CN), cyanate (—CNO), thiocyanoate (—SCN), and thioisocyanato (—NCS)
through a continuous flow microfluidic electrochemical reactor in the presence of a base, one of a halide salt or pseudohalide salt (MY), and a mediator;
applying an electrical current through the continuous flow microfluidic electrochemical reactor; and
performing a single pass oxidative addition to create a geminal dipseudohalide or halide-pseudohalide compound of the general Formula II

OG Complex Work Unit Chemistry
wherein for Formula II, R1 and R2 are any combination of H, methyl (—CH3), ethyl (—CH2CH3), propyl (—CH2CH2CH3), hydroxy (—OH), methoxy (—CH2OH), ethoxy (—CH2CH2OH), methyl ester (—CH2COOCH3), propyl methyl ester (—CH2CH2COOCH3), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidine, oxetane, 2,2-dimethyl-1,3,dioxane, and phenyl, and X is a pseudohalide moiety selected from the group consisting of nitro (—NO2), cyano (—CN), cyanate (—CNO), thiocyanoate (—SCN), and thioisocyanato (—NCS) and Y is a nitro (—NO), cyano (—CN), cyanate (—CNO), thiocyanate (—SCN), thioisocyanate (—NCS), azido (—N3), chloro (—Cl), or bromo (—Br) functional group.