DC Field | Value | Language |
---|---|---|
dc.contributor.author | Xie, Weilong | ko |
dc.contributor.author | Heo, Joon | ko |
dc.contributor.author | Kim, Dongwook | ko |
dc.contributor.author | Chang, Sukbok | ko |
dc.date.accessioned | 2020-05-22T05:20:06Z | - |
dc.date.available | 2020-05-22T05:20:06Z | - |
dc.date.created | 2020-05-18 | - |
dc.date.created | 2020-05-18 | - |
dc.date.created | 2020-05-18 | - |
dc.date.issued | 2020-04 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.16, pp.7487 - 7496 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/274257 | - |
dc.description.abstract | Construction of carbon-carbon bonds is one of the most important tools in chemical synthesis. In the previously established cross-coupling reactions, prefunctionalized starting materials were usually employed in the form of aryl or alkyl (pseudo)halides or their metalated derivatives. However, the direct use of arenes and alkanes via a 2-fold oxidative C-H bond activation strategy to access chemoselective C(sp(2))-C(sp(3)) cross-couplings is highly challenging due to the low reactivity of carbon-hydrogen (C-H) bonds and the difficulty in suppressing side reactions such as homocouplings. Herein, we present the new development of a copper-catalyzed cross-dehydrogenative coupling of polyfluoroarenes with alkanes under mild conditions. Relatively weak sp(3) C-H bonds at the benzylic or allylic positions, and nonactivated hydrocarbons could be alkylated by the newly developed catalyst system. A moderate-to-high site selectivity was observed among various C-H bonds present in hydrocarbon reactants, including gaseous feedstocks and complex molecules. Mechanistic information was obtained by performing combined experimental and computational studies to reveal that the copper catalyst plays a dual role in activating both alkane sp(3) C-H bonds and sp(2) polyfluoroarene C-H bonds. It was also suggested that the noncovalent p-p interaction and weak hydrogen bonds formed in situ between the optimal ligand and arene substrates are key to facilitating the current coupling reactions. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Copper-Catalyzed Direct C-H Alkylation of Polyfluoroarenes by Using Hydrocarbons as an Alkylating Source | - |
dc.type | Article | - |
dc.identifier.wosid | 000529156100036 | - |
dc.identifier.scopusid | 2-s2.0-85088949699 | - |
dc.type.rims | ART | - |
dc.citation.volume | 142 | - |
dc.citation.issue | 16 | - |
dc.citation.beginningpage | 7487 | - |
dc.citation.endingpage | 7496 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.0c00169 | - |
dc.contributor.localauthor | Chang, Sukbok | - |
dc.contributor.nonIdAuthor | Xie, Weilong | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | ELECTRON-DEFICIENT | - |
dc.subject.keywordPlus | DIRECT ARYLATION | - |
dc.subject.keywordPlus | ARYL BROMIDES | - |
dc.subject.keywordPlus | FLUORINE | - |
dc.subject.keywordPlus | FUNCTIONALIZATION | - |
dc.subject.keywordPlus | ALLYLATION | - |
dc.subject.keywordPlus | CHLORIDES | - |
dc.subject.keywordPlus | BONDS | - |
dc.subject.keywordPlus | PHARMACEUTICALS | - |
dc.subject.keywordPlus | ALKENYLATION | - |
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