Synthesis of Hydrazine Derivatives (Hydrazones, Hydrazides)

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Alkylation of hydrazine using a polyanion strategy provides a fast and convenient access to multialkylated hydrazine derivatives. Scope and limitations of the new method are also investigated.
A. Bredihhin, U. Mäeorg, Org. Lett., 2007, 9, 4975-4977.

A. Bredihhin, U. Mäeorg, Org. Lett., 2007, 9, 4975-4977.

Formation and use of a nitrogen dianion for selective hydrazine alkylation provides a fast and easy access to substituted hydrazines, which are widely used as drugs, pesticides, and precursors for a variety of compounds in organic synthesis.
A. Bredihhin, U. M. Groth, U. Mäeorg, Org. Lett., 2007, 9, 1097-1099.

A. Bredihhin, U. M. Groth, U. Mäeorg, Org. Lett., 2007, 9, 1097-1099.

A mild, copper-catalyzed addition of aryl- and heteroarylboronic acids to azo compounds is described. Excellent regioselectivity was observed in the addition to unsymmetrical azo compounds.
K. Kisseljova, O. Tšubrik, R. Sillard, S. Mäeorg, U. Mäeorg, Org. Lett., 2006, 8, 43-45.

K. Kisseljova, O. Tšubrik, R. Sillard, S. Mäeorg, U. Mäeorg, Org. Lett., 2006, 8, 43-45.

Excellent regioselectivity is observed in the addition of diverse organometallic nucleophiles to unsymmetrical azo compounds. Primary/secondary/tertiary alkyl, aryl and heteroaryl substituents were introduced this way in high yields.
O. Tšubrik, R. Sillard, U. Mäeorg, Synthesis, 2006, 843-846.

A highly chemo- and regioselective allylic amination of various hydrazones and hydrazides with allylic carbonates proceeds at ambient temperature in the presence of an [Ir(COD)Cl]₂/pyridine catalyst, ammonium iodide, and diethylzinc to afford the corresponding N-allylation products in high yields.
R. Matunas, A. J. Lai, C. Lee, Tetrahedron, 2005, 61, 6298-9308.