NDLI: Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol† †Electronic supplementary information (ESI) available: Optimization data, experimental procedures, characterization of new compounds, computational methods and spectral data (PDF). See DOI: 10.1039/c8sc021

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Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol† †Electronic supplementary information (ESI) available: Optimization data, experimental procedures, characterization of new compounds, computational methods and spectral data (PDF). See DOI: 10.1039/c8sc021

Content Provider	Semantic Scholar
Author	Richmond, Edward Yi, Jing Vuković, Vuk D. Sajadi, Fatima Rowley, Christopher N. Moran, Joseph
Copyright Year	2018
Abstract	Ring-opening hydroarylation of cyclopropanes is typically limited to substrates bearing a donor-acceptor motif. Here, the transformation is achieved for monosubstituted cyclopropanes by using catalytic Brønsted acid in hexafluoroisopropanol (HFIP) solvent, constituting a rare example where such cyclopropanes engage in intermolecular C-C bond formation. Branched products are obtained when electron-rich arylcyclopropanes react with a broad scope of arene nucleophiles in accord with a simple SN1-type ring-opening mechanism. In contrast, linear products are obtained when cyclopropylketones react with electron-rich arene nucleophiles. In the latter case, mechanistic experiments and DFT-calculations support a homo-conjugate addition pathway.
Starting Page	6411
Ending Page	6416
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/c8sc02126k
PubMed reference number	30310570
Journal	Medline
Volume Number	9
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2018/sc/c8sc02126k
Alternate Webpage(s)	http://www.rsc.org/suppdata/c8/sc/c8sc02126k/c8sc02126k1.pdf
Alternate Webpage(s)	https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/cc/f4/SC-009-C8SC02126K.PMC6115651.pdf
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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