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Chem Commun (Camb). 2004 Mar 21;(6):704-5. Epub 2004 Feb 13.

Synthesis and structural characterization of an azatitanacyclobutene: the key intermediate in the catalytic anti-Markovnikov addition of primary amines to [small alpha]-alkynes.

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1
Laboratoire de Chimie Organométallique et de Catalyse, Institut Le Bel, Université Louis Pasteur, Strasbourg, France.

Abstract

Reaction of the imidotitanium complexes [Ti(N(t)Bu)(N(2)N(py))(py)](1) and [Ti(N-2,6-C(6)H(3)(i)Pr(2))(N(2)N(py))(py)](2) with phenyl acetylene and tolyl acetylene in toluene gave the corresponding [2+2] cycloaddition products [Ti(N(2)N(py))[kappa(2)-N((t)Bu)CH[double bond]CR]](R = Ph:3, Tol:4) and [Ti(N(2)N(py))[kappa(2)-N(2,6-C(6)H(3)(i)Pr(2))CH[double bond]CR]](R = Ph:5, Tol: 6). Complex 6 is the first example of a key intermediate in the anti-Markovnikov addition of a primary amine to a terminal acetylene which has been structurally characterized by X-ray diffraction.

PMID:
15010790
DOI:
10.1039/b316383k
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