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Volume 220, 2019
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Isolation of a C3-metalated indolizine complex and a phosphonium ring-fused bicyclic metallafuran from the osmium-induced transformation of pyridine-tethered alkynes

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Abstract

The first C3-metalated indolizine complex was prepared from the reaction between cis-[Os(dppm)2Cl2] (dppm = 1,1-bis(diphenylphosphino)methane) and propargylic pyridine, HC[triple bond, length as m-dash]CC(OH)(2-py)2. A phosphonium ring-fused bicyclic osmafuran complex was also prepared from the reaction between cis-[Os(dppm)2Cl2] and pyridyl ynone, HC[triple bond, length as m-dash]C(C[double bond, length as m-dash]O)(2-py). The formation of these two products revealed the intermediacy of metal–vinylidene species regarding [Os(dppm)2Cl]+-mediated alkyne transformations. Comparison of the d6 transition-metal precursors employed to activate HC[triple bond, length as m-dash]CC(OH)(2-py)2 suggests that precursors with higher π-basicity favor the vinylidene-involving pathway.

Graphical abstract: Isolation of a C3-metalated indolizine complex and a phosphonium ring-fused bicyclic metallafuran from the osmium-induced transformation of pyridine-tethered alkynes

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Submitted
25 Apr 2019
Accepted
14 May 2019
First published
25 Jun 2019

Faraday Discuss., 2019,220, 196-207
Article type
Paper

Isolation of a C3-metalated indolizine complex and a phosphonium ring-fused bicyclic metallafuran from the osmium-induced transformation of pyridine-tethered alkynes

L. Chung, C. Yeung, H. Shek and C. Wong, Faraday Discuss., 2019, 220, 196
DOI: 10.1039/C9FD00048H

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