In Situ Catalyst Generation and Benchtop-Compatible Entry Points for TiII/TiIV Redox Catalytic Reactions

Zachary W. Davis-Gilbert, Kento Kawakita, Daniel R. Blechschmidt, Hayato Tsurugi, Kazushi Mashima, Ian A. Tonks

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

The development of several in situ generated catalyst systems for Ti-catalyzed oxidative nitrene transfer reactions is reported. The simplest and widely applicable catalyst system, TiCl4(THF)2/Zn0, can be set up on the benchtop under air. This system uses commercially available reagents and can be used as an entry point for TiII/TiIV multicomponent redox reactions for the synthesis of pyrroles, α,γ-unsaturated imines, α,β-unsaturated imines, cyclopropylimines, and arenes.

Original languageEnglish (US)
Pages (from-to)4439-4445
Number of pages7
JournalOrganometallics
Volume37
Issue number23
DOIs
StatePublished - Dec 10 2018

Bibliographical note

Funding Information:
We would like to thank John E. Ellis (UMN) for synthesizing the TiCl4(THF)2 used in this work. Financial support was provided by the University of Minnesota (Doctoral Dissertation Fellowship to ZWD-G), the National Institutes of Health (1R35GM119457), and the Alfred P. Sloan Foundation (I.A.T. is a 2017 Sloan Fellow). Equipment for the Chemistry Department NMR facility was supported through a grant from the National Institutes of Health (S10OD011952) with matching funds from the University of Minnesota.

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