Alternative reaction pathways in domino reactions of hydrazinediidozirconium complexes with alkynes

Chemistry : a European Journal
Thorsten GehrmannLutz H Gade

Abstract

Reaction of [Zr{(NAr)(2)N(py)}(NMe(2))(2)] (Ar=3,5-xylyl: 2 a, mesityl: 2 b) with one or two molar equivalents of 1,1-diphenylhydrazine gave the mixed amido/hydrazido(1-) complex [Zr{(NMes)(2)N(py)}(HNNPh(2))(NMe(2))] (3), the bis-hydrazido complex [Zr{(NMes)(2)N(py)}(HNNPh(2))(2)] (4), and, in the presence of excess 4-dimethylaminopyridine (DMAP), hexacoordinate hydrazinediidozirconium complexes [Zr{(NXyl)(2)N(py)}(=NN(Me)Ph)(dmap)(2)] (5) and [Zr{(NXyl)(2)N(py)}(=NNPh(2))(dmap)(2)] (6). The reaction of one equivalent of the zirconium-hydrazinediide [Zr{(NTBS)(2)N(py)}(NNPh(2))(py)] (1) with disubstituted alkynes at RT for 16 h led to the formation of seven-membered diazazirconacycles 7 a-7 e in high yields. Similar reactivity was observed by reacting bis-amido complex 2 b with one molar equivalent of the corresponding alkyne and diphenylhydrazine. The formation of the seven-membered zirconacycles implied a key coupling step that involved the alkyne and one of the aryl rings of the diphenylhydrazinediido ligand. In some cases, such as the reaction with 2-butyne, the corresponding metallacycle was only obtained in modest yields (45 % for the reaction with 2-butyne) and a second major product, vinylimido complex 9, was formed in...Continue Reading

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Citations

Aug 1, 2015·Journal of the American Chemical Society·Laura C StevensonPhilip Mountford
Aug 18, 2016·The Journal of Organic Chemistry·Manikandan ThangarajAkkattu T Biju
Feb 13, 2013·Chemistry : a European Journal·Pei Jen TiongPhilip Mountford
Feb 12, 2014·Organic & Biomolecular Chemistry·Ganesh Chandra MidyaJyotirmayee Dash
Aug 25, 2017·Inorganic Chemistry·Benjamin A CloughPhilip Mountford

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