Issue 6, 2004

Synthesis and structural characterization of an azatitanacyclobutene: the key intermediate in the catalytic anti-Markovnikov addition of primary amines to α-alkynes

Abstract

Reaction of the imidotitanium complexes [Ti(NtBu)(N2Npy)(py)] (1) and [Ti(N-2,6-C6H3iPr2)(N2Npy)(py)] (2) with phenyl acetylene and tolyl acetylene in toluene gave the corresponding {2+2} cycloaddition products [Ti(N2Npy){κ2-N(tBu)CH[double bond, length as m-dash]CR}] (R = Ph: 3, Tol: 4) and [Ti(N2Npy){κ2-N(2,6-C6H3iPr2)CH[double bond, length as m-dash]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.

Graphical abstract: Synthesis and structural characterization of an azatitanacyclobutene: the key intermediate in the catalytic anti-Markovnikov addition of primary amines to α-alkynes

Supplementary files

Article information

Article type
Communication
Submitted
16 Dec 2003
Accepted
20 Jan 2004
First published
13 Feb 2004

Chem. Commun., 2004, 704-705

Synthesis and structural characterization of an azatitanacyclobutene: the key intermediate in the catalytic anti-Markovnikov addition of primary amines to α-alkynes

B. D. Ward, A. Maisse-François, P. Mountford and L. H. Gade, Chem. Commun., 2004, 704 DOI: 10.1039/B316383K

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