Patent ID: 11912704
Assignee: UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.
Field: Organic fine chemistry (Chemistry)
Classification: CPC C | IPC C

Claim 0:
1. A method of synthesizing a bis-allylated compound, the method comprising:
reacting a Knoevenagel adduct and chalcone-derived electrophile in the presence of a palladium catalyst and base at a first reaction temperature for a first reaction time;
wherein the Knoevenagel adduct has a formula represented by a structure:, wherein each of R1a, R1b, R1c, R1d, R1e and K1f is independently selected from hydrogen, halogens, and C1-C8 alkyl; or wherein each of R1a, R1b, R1e and R1f is independently selected from hydrogen and C1-C8 alkyl, and wherein R1c and R1d are optionally combined and form a C3 to C8 cycloalkyl, C3 to C8 cycloalkenyl, or 5-atom or 6-atom heterocycle containing one or more oxygens;
wherein the chalcone-derived electrophile has a formula represented by a structure:, wherein Ar1 is a phenyl group optionally substituted with 1, 2, or 3 groups that are electron-withdrawing or electron-donating; and
wherein Ar2 is a phenyl group optionally substituted with 1, 2, or 3 groups that are electron-withdrawing or electron-donating; and
wherein at least one of Ar1 and Ar2 is substituted with 1, 2, or 3 groups that are electron-withdrawing or electron-donating;
after completion of the first reaction time, adding to the reaction an allylic electrophile and continuing the reaction at second reaction temperature for a second reaction time, wherein the allylic electrophile has a formula represented by a structure:, wherein X is a halogen; and wherein R3 is selected from hydrogen and C1-C8 alkyl;
thereby synthesizing the bis-allylated compound, wherein the bis-allylated compound has a formula represented by a structure:,