Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenesElectronic supplementary information (ESI) available: Experimental details and spectral data are provided. CCDC 1860899 and 1860900 (6aF-Me2), 1860901 and 1860902 (7aF-Me2), and 1860904 and 1860905 (11A-Me2). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc03525c
The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [ c ]carbazoles. Using benzene, pyrrole, and indole derivatives as the nucleophiles, benzo[ c ]-, pyrrolo[2,3- c ]-, and indolo[2,3- c ]carbazoles were produced, respectively. The reaction proceeded...
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| creator | Kawada, Yuiki Ohmura, Shunsuke Kobayashi, Misaki Nojo, Wataru Kondo, Masaki Matsuda, Yuka Matsuoka, Junpei Inuki, Shinsuke Oishi, Shinya Wang, Chao Saito, Tatsuo Uchiyama, Masanobu Suzuki, Takanori Ohno, Hiroaki |
| description | The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [
c
]carbazoles. Using benzene, pyrrole, and indole derivatives as the nucleophiles, benzo[
c
]-, pyrrolo[2,3-
c
]-, and indolo[2,3-
c
]carbazoles were produced, respectively. The reaction proceeded through pyrrole and benzene ring construction accompanied by the formation of two carbon-carbon and one carbon-nitrogen bond and the cleavage of two aromatic C-H bonds. The mechanism of the reaction with pyrrole was investigated by density functional theory calculations.
N
,
N
′-dimethylated indolo[2,3-
c
]carbazole showed dual ultraviolet-visible-near-infrared and fluorescence spectral changes upon electrolysis.
The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [
c
]carbazoles. |
| doi_str_mv | 10.1039/c8sc03525c |
| format | Article |
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c
]carbazoles. Using benzene, pyrrole, and indole derivatives as the nucleophiles, benzo[
c
]-, pyrrolo[2,3-
c
]-, and indolo[2,3-
c
]carbazoles were produced, respectively. The reaction proceeded through pyrrole and benzene ring construction accompanied by the formation of two carbon-carbon and one carbon-nitrogen bond and the cleavage of two aromatic C-H bonds. The mechanism of the reaction with pyrrole was investigated by density functional theory calculations.
N
,
N
′-dimethylated indolo[2,3-
c
]carbazole showed dual ultraviolet-visible-near-infrared and fluorescence spectral changes upon electrolysis.
The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [
c
]carbazoles.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c8sc03525c</identifier><language>eng</language><creationdate>2018-11</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,860,27901,27902</link.rule.ids></links><search><creatorcontrib>Kawada, Yuiki</creatorcontrib><creatorcontrib>Ohmura, Shunsuke</creatorcontrib><creatorcontrib>Kobayashi, Misaki</creatorcontrib><creatorcontrib>Nojo, Wataru</creatorcontrib><creatorcontrib>Kondo, Masaki</creatorcontrib><creatorcontrib>Matsuda, Yuka</creatorcontrib><creatorcontrib>Matsuoka, Junpei</creatorcontrib><creatorcontrib>Inuki, Shinsuke</creatorcontrib><creatorcontrib>Oishi, Shinya</creatorcontrib><creatorcontrib>Wang, Chao</creatorcontrib><creatorcontrib>Saito, Tatsuo</creatorcontrib><creatorcontrib>Uchiyama, Masanobu</creatorcontrib><creatorcontrib>Suzuki, Takanori</creatorcontrib><creatorcontrib>Ohno, Hiroaki</creatorcontrib><title>Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenesElectronic supplementary information (ESI) available: Experimental details and spectral data are provided. CCDC 1860899 and 1860900 (6aF-Me2), 1860901 and 1860902 (7aF-Me2), and 1860904 and 1860905 (11A-Me2). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc03525c</title><description>The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [
c
]carbazoles. Using benzene, pyrrole, and indole derivatives as the nucleophiles, benzo[
c
]-, pyrrolo[2,3-
c
]-, and indolo[2,3-
c
]carbazoles were produced, respectively. The reaction proceeded through pyrrole and benzene ring construction accompanied by the formation of two carbon-carbon and one carbon-nitrogen bond and the cleavage of two aromatic C-H bonds. The mechanism of the reaction with pyrrole was investigated by density functional theory calculations.
N
,
N
′-dimethylated indolo[2,3-
c
]carbazole showed dual ultraviolet-visible-near-infrared and fluorescence spectral changes upon electrolysis.
The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [
c
]carbazoles.</description><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFUcFKxDAQraKgqBfvwnjrgl3T1q5bb9LdxT2IB72JLLPJrEZiUpIq1r_xT52t4gqC5pJh3st7byZRtJ-Kfiry8lgOgxR5kRVyPdrOxEmaDIq83PiuM7EV7YXwKPjkeVpkp9tr7yPtSTYQWts8UNAB3ALQtyZBa58NNqTgVt5J9HN8c4YCzFu4d0bFupdIbNC0gSkSg0RF4Allo53tVN60okTp1vIrtIplicuxYT_vrJYQnuva0BPZhh1B24XzT9g9j8fX0x7gC2qDc0NnMH6tyeuOakBRw8CnaKiXcssmh1laQO3dCzurPlTVqIJ0OBDDsuzIy7oUAuIBTpJLynpHX630B5xBfPoNr9onP-oC4jQ97yh9mDgPHLeDpW8DJzTu3mP9wCN2qbSFajoB5jlesgdareBzZAhEMLqansHvv9yNNhdoAu193TvRwWR8U10kPshZzTvh3c1W9HwnOvwLn9Vqkf-n8QHnx7dk</recordid><startdate>20181114</startdate><enddate>20181114</enddate><creator>Kawada, Yuiki</creator><creator>Ohmura, Shunsuke</creator><creator>Kobayashi, Misaki</creator><creator>Nojo, Wataru</creator><creator>Kondo, Masaki</creator><creator>Matsuda, Yuka</creator><creator>Matsuoka, Junpei</creator><creator>Inuki, Shinsuke</creator><creator>Oishi, Shinya</creator><creator>Wang, Chao</creator><creator>Saito, Tatsuo</creator><creator>Uchiyama, Masanobu</creator><creator>Suzuki, Takanori</creator><creator>Ohno, Hiroaki</creator><scope/></search><sort><creationdate>20181114</creationdate><title>Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenesElectronic supplementary information (ESI) available: Experimental details and spectral data are provided. CCDC 1860899 and 1860900 (6aF-Me2), 1860901 and 1860902 (7aF-Me2), and 1860904 and 1860905 (11A-Me2). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc03525c</title><author>Kawada, Yuiki ; Ohmura, Shunsuke ; Kobayashi, Misaki ; Nojo, Wataru ; Kondo, Masaki ; Matsuda, Yuka ; Matsuoka, Junpei ; Inuki, Shinsuke ; Oishi, Shinya ; Wang, Chao ; Saito, Tatsuo ; Uchiyama, Masanobu ; Suzuki, Takanori ; Ohno, Hiroaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c8sc03525c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kawada, Yuiki</creatorcontrib><creatorcontrib>Ohmura, Shunsuke</creatorcontrib><creatorcontrib>Kobayashi, Misaki</creatorcontrib><creatorcontrib>Nojo, Wataru</creatorcontrib><creatorcontrib>Kondo, Masaki</creatorcontrib><creatorcontrib>Matsuda, Yuka</creatorcontrib><creatorcontrib>Matsuoka, Junpei</creatorcontrib><creatorcontrib>Inuki, Shinsuke</creatorcontrib><creatorcontrib>Oishi, Shinya</creatorcontrib><creatorcontrib>Wang, Chao</creatorcontrib><creatorcontrib>Saito, Tatsuo</creatorcontrib><creatorcontrib>Uchiyama, Masanobu</creatorcontrib><creatorcontrib>Suzuki, Takanori</creatorcontrib><creatorcontrib>Ohno, Hiroaki</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kawada, Yuiki</au><au>Ohmura, Shunsuke</au><au>Kobayashi, Misaki</au><au>Nojo, Wataru</au><au>Kondo, Masaki</au><au>Matsuda, Yuka</au><au>Matsuoka, Junpei</au><au>Inuki, Shinsuke</au><au>Oishi, Shinya</au><au>Wang, Chao</au><au>Saito, Tatsuo</au><au>Uchiyama, Masanobu</au><au>Suzuki, Takanori</au><au>Ohno, Hiroaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenesElectronic supplementary information (ESI) available: Experimental details and spectral data are provided. CCDC 1860899 and 1860900 (6aF-Me2), 1860901 and 1860902 (7aF-Me2), and 1860904 and 1860905 (11A-Me2). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc03525c</atitle><date>2018-11-14</date><risdate>2018</risdate><volume>9</volume><issue>44</issue><spage>8416</spage><epage>8425</epage><pages>8416-8425</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [
c
]carbazoles. Using benzene, pyrrole, and indole derivatives as the nucleophiles, benzo[
c
]-, pyrrolo[2,3-
c
]-, and indolo[2,3-
c
]carbazoles were produced, respectively. The reaction proceeded through pyrrole and benzene ring construction accompanied by the formation of two carbon-carbon and one carbon-nitrogen bond and the cleavage of two aromatic C-H bonds. The mechanism of the reaction with pyrrole was investigated by density functional theory calculations.
N
,
N
′-dimethylated indolo[2,3-
c
]carbazole showed dual ultraviolet-visible-near-infrared and fluorescence spectral changes upon electrolysis.
The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [
c
]carbazoles.</abstract><doi>10.1039/c8sc03525c</doi><tpages>1</tpages></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| title | Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenesElectronic supplementary information (ESI) available: Experimental details and spectral data are provided. CCDC 1860899 and 1860900 (6aF-Me2), 1860901 and 1860902 (7aF-Me2), and 1860904 and 1860905 (11A-Me2). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc03525c |
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