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Cyclopropanation of Terminal Alkenes via Sequential Atom Transfer Radical Addition – 1,3-Elimination

preprint
submitted on 26.06.2019, 09:27 and posted on 27.06.2019, 15:32 by Nicholas D. C. Tappin, Weronika Michalska, Simon Rohrbach, Philippe Renaud
An operationally simple protocol to affect an atom transfer radical addition (ATRA) of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with tetrabutylammonium fluoride (TBAF). This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated. The whole reaction sequence relies on simple reagents such dilauroyl peroxide (DLP) and TBAF and can be run on multi-gram scales in ethyl acetate as a solvent.

Funding

The Swiss National Science Foundation, Project 200020_172621

History

Email Address of Submitting Author

philippe.renaud@dcb.unibe.ch

Institution

University of Bern

Country

Switzerland

ORCID For Submitting Author

0000-0002-9069-7109

Declaration of Conflict of Interest

No conflict of interest

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