One-step Procedure for the Preparation of oxazolinyl-zinc Complexes by the Atom-efficient Assembly | Chapter 5 | Current Topics on Chemistry and Biochemistry Vol. 3

The present work presents a straightforward, one-pot method for the atom-efficient assembly of three reactive components: a nitrile, an amino alcohol, and a zinc salt, to produce oxazolinyl-zinc complexes. Usually, the synthesis of oxazolinyl metal complexes involves two steps: first, the preparation of the free ligand through condensation of a functionalized nitrile with an amino alcohol in the presence of a Lewis or Brnsted acid catalyst, then a subsequent reaction with metal salts to produce the corresponding metal complexes. Only a few oxazolinyl zinc complexes have been synthesised using this method due to the two-step process's typically poor yield. The presence of Lewis acidic metals in metal-oxazoline complexes makes it feasible for the two processes to be merged.

In a single step, a series of unique chiral organozinc complexes 1 through 15 were built. All crystalline compounds were thoroughly described, and 15 X-ray crystal structures with a broad range of structural variation were reported.

With moderate to high yields (20-90 percent), a number of new chiral organozinc complexes were created in a single step using chiral D/L amino alcohols, nitriles, and a stoichiometric quantity of ZnCl2. A variety of coordination modes, including mono- and bis-chelate complexes, are produced by the reaction, depending on the number of extra donor atoms present, the reaction's stoichiometry, and the kind of -substituent present at the stereogenic centre. The formation of multinuclear complexes was caused by the usage of excessive zinc salt.

Author(s) Details:

Mei Luo,
College of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, People’s Republic of China.

Jing Cheng Zhang,
College of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, People’s Republic of China.

Wen Min Pang,
Department of Chemistry, University of Science and Technology of China, Hefei 230009, People’s Republic of China.

King Kuok Hii,
Department of Chemistry, Imperial College London, Exhibition Road, South Kensington, London SW7 2AZ, UK.

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