Alkyl sulfonyl fluorides as ambiphiles in the stereoselective palladium(II)-catalysed cyclopropanation of unactivated alkenes.

Yilin Cao¹, Warabhorn Rodphon¹, Turki M Alturaifi², Al Vicente Riano D Lisboa¹, Zhouyang Ren¹, Job J C Struijs¹, Hui-Qi Ni¹, Taras Savchuk^3,4, Richard P Loach⁵, Shouliang Yang⁶, Indrawan J McAlpine^6,7, Donna G Blackmond¹, Pavel K Mykhailiuk^3,8, Peng Liu², K Barry Sharpless¹, Keary M Engle¹

¹Department of Chemistry, The Scripps Research Institute, La Jolla, CA USA.

²Department of Chemistry, University of Pittsburgh, Pittsburgh, PA USA.

³Enamine Ltd., Kyiv, Ukraine.

⁴Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine, Kyiv, Ukraine.

⁵Pfizer Medicinal Sciences, Groton, CT USA.

⁶Pfizer Oncology Medicinal Chemistry, San Diego, CA USA.

⁷Genesis Therapeutics, San Diego, CA USA.

⁸Faculty of Chemistry, Taras Shevchenko National University of Kyiv, Kyiv, Ukraine.

PubMed PMC DOI PDF

Abstract

Here we present the ambiphilic reactivity of alkyl sulfonyl fluorides in the stereoselective synthesis of diverse cyclopropanes from olefins, under palladium(II) catalysis. The sulfonyl fluoride functionality serves as both an acidifying group and an internal oxidant within the ambiphile, enabling successive carbopalladation and oxidative addition steps in the catalytic cycle, respectively. The tr…

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