Matches in SemOpenAlex for { <https://semopenalex.org/work/W4385295886> ?p ?o ?g. }
- W4385295886 endingPage "17397" @default.
- W4385295886 startingPage "17389" @default.
- W4385295886 abstract "Herein, we disclose an approach to synthesize tert-alkyl cyclopropanes by leveraging C–F bond functionalization of gem-difluorocyclopropenes using tris(pentafluorophenyl)borane catalysis. The reaction proceeds through the intermediacy of a fluorocyclopropenium ion, which was confirmed by the isolation of [Ph2(C6D5)C3]+[(C6F5)3BF]−. We found that silylketene acetal nucleophiles were optimal reaction partners with fluorocyclopropenium ion intermediates yielding fully substituted cyclopropenes functionalized with two α-tert-alkyl centers (63–93% yield). The regioselectivity of the addition to cyclopropenium ions is controlled by their steric and electronic properties and enables access to 3,3-bis(difluoromethyl)cyclopropenes in short order. The resulting cyclopropene products are readily reduced to the corresponding orphaned cyclopropanes under hydrogenation conditions. Quantum chemical calculations reveal the nature of the C–F bond cleavage steps and provide evidence for catalysis by boron and not silylated oxonium ions, though Si–F bond formation is the enthalpic driving force for the reaction." @default.
- W4385295886 created "2023-07-28" @default.
- W4385295886 creator A5023552588 @default.
- W4385295886 creator A5039366956 @default.
- W4385295886 creator A5043200844 @default.
- W4385295886 creator A5050414026 @default.
- W4385295886 creator A5057241908 @default.
- W4385295886 date "2023-07-26" @default.
- W4385295886 modified "2023-10-16" @default.
- W4385295886 title "Borane-Catalyzed C–F Bond Functionalization of <i>gem</i>-Difluorocyclopropenes Enables the Synthesis of Orphaned Cyclopropanes" @default.
- W4385295886 cites W1964284609 @default.
- W4385295886 cites W1968818053 @default.
- W4385295886 cites W1987717909 @default.
- W4385295886 cites W1988091937 @default.
- W4385295886 cites W1993256265 @default.
- W4385295886 cites W2008628207 @default.
- W4385295886 cites W2011215428 @default.
- W4385295886 cites W2014138834 @default.
- W4385295886 cites W2019924321 @default.
- W4385295886 cites W2024777137 @default.
- W4385295886 cites W2030380295 @default.
- W4385295886 cites W2033990154 @default.
- W4385295886 cites W2034151368 @default.
- W4385295886 cites W2035013891 @default.
- W4385295886 cites W2037570317 @default.
- W4385295886 cites W2049996223 @default.
- W4385295886 cites W2051681766 @default.
- W4385295886 cites W2052652634 @default.
- W4385295886 cites W2054473656 @default.
- W4385295886 cites W2057386922 @default.
- W4385295886 cites W2058721011 @default.
- W4385295886 cites W2061081886 @default.
- W4385295886 cites W2064811421 @default.
- W4385295886 cites W2069617573 @default.
- W4385295886 cites W2070005238 @default.
- W4385295886 cites W2076311795 @default.
- W4385295886 cites W2082917109 @default.
- W4385295886 cites W2089867387 @default.
- W4385295886 cites W2110939537 @default.
- W4385295886 cites W2112850441 @default.
- W4385295886 cites W2118585686 @default.
- W4385295886 cites W2171916990 @default.
- W4385295886 cites W2313860249 @default.
- W4385295886 cites W2319757463 @default.
- W4385295886 cites W2330304021 @default.
- W4385295886 cites W2335376314 @default.
- W4385295886 cites W2422726141 @default.
- W4385295886 cites W2479259081 @default.
- W4385295886 cites W2555513080 @default.
- W4385295886 cites W2583844778 @default.
- W4385295886 cites W2606693751 @default.
- W4385295886 cites W2611749692 @default.
- W4385295886 cites W2887414248 @default.
- W4385295886 cites W2890406878 @default.
- W4385295886 cites W2911997094 @default.
- W4385295886 cites W2949256104 @default.
- W4385295886 cites W2949920827 @default.
- W4385295886 cites W2951299057 @default.
- W4385295886 cites W2952015901 @default.
- W4385295886 cites W2952330700 @default.
- W4385295886 cites W2953221764 @default.
- W4385295886 cites W2955949443 @default.
- W4385295886 cites W2999150426 @default.
- W4385295886 cites W3006234984 @default.
- W4385295886 cites W3008144924 @default.
- W4385295886 cites W3012620675 @default.
- W4385295886 cites W3013582981 @default.
- W4385295886 cites W3020719222 @default.
- W4385295886 cites W3026879981 @default.
- W4385295886 cites W3041515390 @default.
- W4385295886 cites W3043866112 @default.
- W4385295886 cites W3085869156 @default.
- W4385295886 cites W3118401117 @default.
- W4385295886 cites W3121131000 @default.
- W4385295886 cites W3134454495 @default.
- W4385295886 cites W3153685568 @default.
- W4385295886 cites W3177009667 @default.
- W4385295886 cites W3212829051 @default.
- W4385295886 cites W4206146471 @default.
- W4385295886 cites W4210593013 @default.
- W4385295886 cites W4213072928 @default.
- W4385295886 cites W4225386977 @default.
- W4385295886 cites W4229056577 @default.
- W4385295886 cites W4280564133 @default.
- W4385295886 cites W4283317658 @default.
- W4385295886 cites W4290660657 @default.
- W4385295886 cites W4294992517 @default.
- W4385295886 cites W4295756814 @default.
- W4385295886 cites W4297517751 @default.
- W4385295886 cites W4297873124 @default.
- W4385295886 cites W4307715067 @default.
- W4385295886 cites W4313829400 @default.
- W4385295886 cites W4361290875 @default.
- W4385295886 cites W4367176907 @default.
- W4385295886 cites W4376271968 @default.
- W4385295886 cites W4382653187 @default.
- W4385295886 doi "https://doi.org/10.1021/jacs.3c05278" @default.
- W4385295886 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37494703" @default.