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

doi:10.1021/acs.organomet.8b00474

In Situ Catalyst Generation and Benchtop-Compatible Entry Points for Ti^II/Ti^IV Redox Catalytic Reactions

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

25 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 Ti^II/Ti^IV multicomponent redox reactions for the synthesis of pyrroles, α,γ-unsaturated imines, α,β-unsaturated imines, cyclopropylimines, and arenes.

Original language	English (US)
Pages (from-to)	4439-4445
Number of pages	7
Journal	Organometallics
Volume	37
Issue number	23
DOIs	https://doi.org/10.1021/acs.organomet.8b00474
State	Published - 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.

Publisher Copyright:
© 2018 American Chemical Society.

Publisher link

10.1021/acs.organomet.8b00474

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6892472

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

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.",

author = "Davis-Gilbert, {Zachary W.} and Kento Kawakita and Blechschmidt, {Daniel R.} and Hayato Tsurugi and Kazushi Mashima and Tonks, {Ian A.}",

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. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Davis-Gilbert, Zachary W.

AU - Kawakita, Kento

AU - Blechschmidt, Daniel R.

AU - Tsurugi, Hayato

AU - Mashima, Kazushi

AU - Tonks, Ian A.

N1 - 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. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/12/10

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AB - 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.

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