Functionalization of Benzylic C(sp3)H Bonds of Heteroaryl Aldehydes through N-Heterocyclic Carbene Organocatalysis
Aryl aldehyde activation: Oxidative activation of 2‐methylindole‐3‐carboxaldehyde (I) through N‐heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho‐quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2013-10, Vol.52 (42), p.11134-11137 |
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| container_end_page | 11137 |
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| container_issue | 42 |
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| container_title | Angewandte Chemie International Edition |
| container_volume | 52 |
| creator | Chen, Xingkuan Yang, Song Song, Bao-An Chi, Yonggui Robin |
| description | Aryl aldehyde activation: Oxidative activation of 2‐methylindole‐3‐carboxaldehyde (I) through N‐heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho‐quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary carbon center. |
| doi_str_mv | 10.1002/anie.201305861 |
| format | Article |
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This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary carbon center.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201305861</identifier><identifier>PMID: 24038663</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehydes - chemistry ; Benzyl Compounds - chemistry ; C-H functionalization ; Catalysis ; indoles ; Indoles - chemistry ; Methane - analogs & derivatives ; Methane - chemistry ; Molecular Structure ; N-heterocyclic carbenes ; Spiro Compounds ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2013-10, Vol.52 (42), p.11134-11137</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. 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Chem. Int. Ed</addtitle><date>2013-10-11</date><risdate>2013</risdate><volume>52</volume><issue>42</issue><spage>11134</spage><epage>11137</epage><pages>11134-11137</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Aryl aldehyde activation: Oxidative activation of 2‐methylindole‐3‐carboxaldehyde (I) through N‐heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho‐quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary carbon center.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24038663</pmid><doi>10.1002/anie.201305861</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record> |
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| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2013-10, Vol.52 (42), p.11134-11137 |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Aldehydes - chemistry Benzyl Compounds - chemistry C-H functionalization Catalysis indoles Indoles - chemistry Methane - analogs & derivatives Methane - chemistry Molecular Structure N-heterocyclic carbenes Spiro Compounds synthetic methods |
| title | Functionalization of Benzylic C(sp3)H Bonds of Heteroaryl Aldehydes through N-Heterocyclic Carbene Organocatalysis |
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