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Activation and Functionalization of C–C σ-Bonds of Alkylidene Cyclopropanes at Main Group Centers

preprint
revised on 03.04.2020 and posted on 06.04.2020 by Mark Crimmin, Richard Y Kong
Aluminum(I) and magnesium(I) compounds are reported for the C–C s-bond activation of strained alkylidene cyclopropanes. These reactions result in the formal addition of the C–C s-bond to main group center either at a single site (Al) or across a metal–metal bond (Mg–Mg). Mechanistic studies suggest that rather than occurring by a concerted oxidative addition, these reactions involve stepwise processes in which substrate binding to the main group metal acts as a precursor to a- or b-alkyl migration steps that break the C–C s-bond. This mechanistic understanding is used to develop the magnesium-catalyzed hydrosilylation of the C–C s-bonds of alkylidene cyclopropanes.

Funding

We are grateful to the ERC (FluoroFix: 677367) for generous funding. We thank Imperial College London for the award of a President’s Scholarship (RYK).

History

Email Address of Submitting Author

m.crimmin@imperial.ac.uk

Institution

Imperial College London

Country

United Kingdom

ORCID For Submitting Author

0000-0002-9339-9182

Declaration of Conflict of Interest

Authors declare no conflicts of interest

Version Notes

Version 1.1 - The SI has been updated to include kinetics data

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