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US 12,076,715 B1Granted
Synthesis and characterization of air-stable iron-based catalysts for Suzuki-Miyaura cross-coupling reactions of alkyl halides and aryl boronic esters
AssigneeThe Trustees of Boston College
InventorsAlexander Wong, Jeffery Byers
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Abstract
This disclosure relates to novel catalysts for Suzuki-Miyaura cross-coupling reactions, the use thereof, and the methods of making the same.
Claims20
An iron(III) catalyst for Suzuki-Miyaura cross-coupling reactions, wherein the catalyst has a composition according to Formula 1:
- wherein:
- each R1 is independently selected from the group consisting of H, an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, or phenyl, and an alkyl substituted aryl group wherein the alkyl group has 1 to 5 carbon atoms;
- each R2 is independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and an alkyl substituted aryl group wherein the alkyl group has 1 to 5 carbon atom;
- and
- each R3 is independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and an alkyl substituted aryl wherein the alkyl group has 1 to 5 carbon atoms.
2 more elements
An iron(III) catalyst-for Suzuki-Miyaura cross-coupling reactions, wherein the catalyst has a composition according to Formula 1:
- wherein:
- each R1 is independently selected from the group consisting of H, an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and a substituted aryl group;
- each R2 is independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and a substituted aryl group;
- and
- each R3 is independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and a substituted aryl,
- wherein the substituted aryl group is selected from the group consisting of 2,6-dialkyl substituted aryl, 3,5-dialkyl substituted aryl, 2,4,6-trialkyl substituted aryl, and 2,4,6-trisubstituted aryl, wherein in the 2,4,6-trisubstituted aryl groups a 2-substituent and a 6-substituent are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, isopropyl, neopentyl, tert-butyl, cyclopentyl, cyclopropyl, and CF3, and a 4-substituent is selected from the group consisting of a halogen, an alkyl ether, and a dialkyl amine, wherein the alkyl comprises a group selected from methyl, ethyl, propyl, butyl, pentyl, isopropyl, neopentyl, tert-butyl, cyclopentyl, cyclopropyl, and CF3.
3 more elements
A method of making an iron(III) catalyst for Suzuki-Miyaura cross-coupling reactions comprising the steps of:
- preparing a solution of an Fe(acac)3 complex;
- reacting a β-diketimine compound with butyllithium to form a β-diketiminate;
- mixing the β-diketiminate and the solution of an Fe(acac)3 complex to form the iron(III) catalyst having a composition according to Formula 1:
- wherein;
- each R1 is independently selected from the group consisting of H, an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and an alkyl substituted aryl group wherein the alkyl group has 1 to 5 carbon atoms;
- each R2 is independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and an alkyl substituted aryl group wherein the alkyl group has 1 to 5 carbon atom;
- and
- each R3 is independently selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, cyclopentyl, cyclopropyl, CF3, phenyl, and an alkyl substituted aryl wherein the alkyl group has 1 to 5 carbon atoms.
5 more elements
Dependencies are inferred from the claim text.