Primary alcohols can be coupled with secondary benzylic alcohols by an air-stable catalytic system involving terpyridine ruthenium or iridium complexes.
a b s t r a c tA deprotonated 2-imidazoline-4(5)-one product ion was observed as a major fragment in the collisioninduced dissociation (CID) of several dipeptides containing serine at the C-terminal and an amino acid with an alkyl substituent at the N-terminal. This fragment becomes predominant at high collision energies. The same type of product ion was seen in the CID of cyclo(GlyGly). Labeling GlySer with O-18 suggests that the fragmentation may proceed through a symmetrical intermediate such as a deprotonated diketopiperazine. Density functional theory calculations of GlySer provided a possible mechanism for the fragmentation.
Alcohols Q 0230Alcohol Cross-Coupling Reactions Catalyzed by Ru and Ir Terpyridine Complexes. -The present green reaction is highly atom economical as it only produces H2O by-product. The system does not need any hydrogen donors or acceptors. -(GNANAMGARI, D.; LEUNG, C. H.; SCHLEY, N. D.; HILTON, S. T.; CRABTREE*, R. H.; Org. Biomol. Chem. 6 (2008) 23, 4442-4445; Dep. Chem., Yale Univ., New Haven, CT 06511, USA; Eng.) -Bartels 17-078
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