Patent ID: 7709654

Claim:
A process for producing an oxazole (I), imidazole (II), or pyrazole (III) boryl compound, the process comprising: (a) reacting an oxazole (IV), imidazole (V), or pyrazole (VI) with an HB or B—B organic compound in a reaction mixture with a non-reactive solvent at a temperature between about 0° C. and 150° C. and in the presence of a catalytically effective amount of an iridium complex catalytic composition, the oxazole (IV), imidazole (V), or pyrazole (VI) having a structure according to formula IV, V, or VI, respectively: wherein: (i) R 1 is independently selected from the group consisting of hydrogen, boryl, halo, cyano, alkyl, alkoxy, thioalkyl, amino alkyl, acyl, alkyl aminoacyl, trifluoro alkyl, aryl, alkyl silyl, and containing 1 to 8 carbon atoms except for the halo group and boryl group, (ii) R 2 is selected from the group consisting of methyl, isopropyl, triisopropylsilyl, phenyl, benzyl, para-methoxybenzyl, tert-butoxycarbonyl, (benzyloxy)carbonyl, N,N-dimethylaminosulfonyl, N,N-dimethylcarboxamide, para-toluenesulfonyl, and 9H-Fluoren-9-ylmethyloxycarbonyl; and (iii) the iridium complex catalytic composition comprises an iridium complex of the formula: (BY) n -lr-(ligand) m , where n is equal to one to five, m is equal to one to three, excluding hydrogen, bonded to the iridium, BY is a boron moiety, the ligand is selected from the group consisting of a phosphorus organic ligand, an organic amine, an imine, a nitrogen heterocycle, and an ether, and the ligand is at least in part bonded to the iridium; (b) forming the oxazole (I), imidazole (II), or pyrazole (III) boryl compound in the reaction mixture, the oxazole (I), imidazole (II), or pyrazole (III) boryl compound having a structure according to formula I, II, or III, respectively: wherein: (i) R 1 is independently selected from the group consisting of hydrogen, boryl, halo, cyano, alkyl, alkoxy, thioalkyl, amino alkyl, acyl, alkyl aminoacyl, trifluoro alkyl, aryl, alkyl silyl, and containing 1 to 8 carbon atoms except for the halo group and boryl group, (ii) R 2 is selected from the group consisting of methyl, isopropyl, triisopropylsilyl, phenyl, benzyl, para-methoxybenzyl, tert-butoxycarbonyl, (benzyloxy)carbonyl, N,N-dimethylaminosulfonyl, N,N-dimethylcarboxamide, para-toluenesulfonyl, and 9H-Fluoren-9-ylmethyloxycarbonyl; and (c) evaporating the solvent and portions of the reaction mixture which are volatile from the reaction mixture to produce the oxazole (I), imidazole (II), or pyrazole (III) boryl compound.