Microwave facilitated allyllic substitution
AssigneePersonal Chemistry I Uppsala AB
InventorsUlf Bremberg, Anders Hallberg, Mats Larhed, Christina Moberg, Nils-Fredrik Kaiser
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Abstract
The present invention is draw to microwave heating of a transition metal-catalysed organic reaction, in which a catalyst complex between a transition metal and an auxiliary ligand or ligands, the ligand being asymmetric or symmetric, monodentate or bidentate, results in highly chemoselective, regioselective, and stereoselective allylic substitution reactions. Molybdenum or palladium complexes form suitable catalytic systems with a plethora of ligands in a variety of solvents for such microwave facilitated nucleophilic substitution reactions.
Claims57
A method of performing a transition metal-catalysed asymmetric allylic substitution reaction, comprising the steps of:
- a) preparing a reaction mixture comprising (i) an allylic substrate which includes the structural element C═C—C—X, where X is a leaving group, (ii) a catalyst complex which includes a transition metal and one or more chiral ligands, and (iii) a nucleophile;
- and
- b) exposing said reaction mixture to microwave energy from a controllable microwave source.
A method for preparing a compound library of products of a transition metal-catalysed allylic substitution reaction, comprising the steps of:
- a) preparing a reaction mixture comprising (i) n different species of allylic substrates which include the structural element C═C—C—X, where X is a leaving group, (ii) a catalyst complex which includes a transition metal and one or more ligands, and (iii) m different nucleophiles, wherein n is an integer in the range of 1-25 and m is an integer in the range of 1-10, with the proviso that the product n×m is at least 2;
- and
- b) exposing said reaction mixture to microwave energy from a controllable microwave source.
A method of performing a microwave promoted allylic substitution reaction which comprises the following steps:
- a) preparing a reaction mixture comprising:
- (i) an allylic substrate which includes the structural element C═C—C—X, where X is a leaving group, (ii) a transition metal-catalyst complex including a C1- or C2-symmetrical chiral ligand, and (iii) a nucleophile;
- and
- b) exposing said reaction mixture to microwave energy from a controllable microwave source.
Dependencies are inferred from the claim text.