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Catalysis

Superelectrophilic Aluminum(III)-Ion Pairs Promote a Distinct Reaction Path for Carbonyl-Olefin Metathesis of Medium-Sized Rings

Abstract

We describe the development of a new catalyst system for carbonyl-olefin ring-closing metathesis reactions that relies on Lewis acidic superelectrophiles and significantly expands the current scope of this transformation to medium-sized rings.
Importantly, these superelectrophiles are shown to promote carbonyl-olefin metathesis via a distinct and unprecedented mechanism.

Content

Version History

Sep 30, 2019 Version 1

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The content is available under CC BY NC ND 4.0 License CreativeCommons.org [opens in a new tab]

DOI

10.26434/chemrxiv.9911783.v1
D O I: 10.26434/chemrxiv.9911783.v1 [opens in a new tab]

Funding

We thank the NIH/National Institute of General Medical Sci-ences (R01-GM118644), the Alfred P. Sloan Foundation, the David and Lucile Packard Foundation and the Camille and Hen-ry Dreyfus Foundation for financial support. R.B.W. thanks the National Science Foundation for a predoctoral fellowship. J.L.G.-L. thanks CONACyT for a postdoctoral fellowship.

Author’s competing interest statement

No conflict of interest

Keywords

carbonyl-olefin metathesis, Lewis acid superelectrophiles

Publication

This content is an early or alternative research output and has not been peer-reviewed at the time of posting.