Synthesis of Ti Complexes Supported by an ortho-Terphenoxide Ligand and Their Applications in Alkyne Hydroamination Catalysis

Steven K. Butler, Ethan P. Ashbrook, Ian A. Tonks

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Abstract

The synthesis of a series of Ti complexes of an aryl-linked bis-phenoxide ligand, 3,3″-di-tert-butyl-5,5″-dimethyl-[1,1′:2′,1″-terphenyl]-2,2″-bis(olate), (TPO)H2, is reported. This ortho-linked terphenyl ligand builds on previously reported meta- and para-linked terphenyl-based ligands, completing the isomeric series of terphenoxide ligands. The 4-coordinate (TPO)Ti(NMe2)2 is an active catalyst for alkyne hydroamination with a variety of arylamines, revealing good regioselectivity in reactions with unsymmetric alkynes. Terminal alkynes such as phenylacetylene undergo additional insertion reactions with the key azatitanacyclobutene intermediates, providing further evidence that Ti aryloxide complexes are susceptible to this further reactivity.

Original languageEnglish (US)
Pages (from-to)1732-1739
Number of pages8
JournalOrganometallics
Volume42
Issue number14
DOIs
StatePublished - Jul 24 2023

Bibliographical note

Funding Information:
Financial support was provided by the National Institutes of Health (R35GM119457). Instrumentation for the University of Minnesota Chemistry NMR facility was supported from a grant through the National Institutes of Health (S10OD011952). X-ray diffraction experiments were performed with a diffractometer purchased through a grant from NSF/MRI (1229400) and the University of Minnesota.

Publisher Copyright:
© 2023 American Chemical Society.

PubMed: MeSH publication types

  • Journal Article

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