Heterocyclic Coupling Catalysts and Methods Related Thereto
AssigneeEmory University
InventorsLanny S. Liebeskind, Matthew Lindale, Pavan Kumar Reddy Gangireddy
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Abstract
This disclosure relates to synthetic coupling methods using a catalytic molecule comprising two bonded atoms wherein one atom is an amide nitrogen and the second atom is not nitrogen or carbon, such as sulfur, such as a sufur amide nitrogen bond, typically in a heterocycle, such as substituted benzoisothiazolones and derivatives thereof, as a catalyst in the transformation of hydroxy group containing compounds to amides, esters, ketones, and other carbon to heteroatom or carbon to carbon transformations.
Claims19
A method of catalyzing a coupling reaction comprising mixing
- a) a compound comprising a hydroxy group,
- b) a trisubstituted phosphite,
- c) a nucleophile, and
- d) a catalytic heterocycle comprising two bonded heteroatoms wherein one heteroatom is a nitrogen and the second heteroatom is not nitrogen,
- under conditions such that a compound is formed comprising the nucleophile in place of the hydroxy group.
A method of forming an amide or ester comprising mixing
- a) a compound comprising a carboxylic acid,
- b) a trialkylphosphite,
- c) an amine or an alcohol,
- d) a catalytic sulfur, amide heterocycle, and
- e) copper under conditions such that an amide or an ester is formed.
A method of forming a ketone comprising mixing
- a) a compound comprising a carboxylic acid,
- b) a trialkylphosphite,
- c) an boronic acid,
- d) a sulfur, amide heterocycle, and
- e) copper under conditions such that a ketone is formed.
Dependencies are inferred from the claim text.