Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules
Benzoxanthenes and their analogues are a very important class of compounds mainly due to their wide range of biological and technological applications. The development of a new methodology for their synthesis, involving an Ullmann-type coupling followed by an intramolecular C–H arylation, catalyzed...
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| Veröffentlicht in: | Journal of organic chemistry 2023-08, Vol.88 (16), p.11552-11561 |
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| container_end_page | 11561 |
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| container_issue | 16 |
| container_start_page | 11552 |
| container_title | Journal of organic chemistry |
| container_volume | 88 |
| creator | Kaplanai, Entzy Tonis, Efstathios Drymona, Maria Zagranyarski, Yulian Tzeli, Demeter Vougioukalakis, Georgios C. |
| description | Benzoxanthenes and their analogues are a very important class of compounds mainly due to their wide range of biological and technological applications. The development of a new methodology for their synthesis, involving an Ullmann-type coupling followed by an intramolecular C–H arylation, catalyzed by copper in a domino fashion, is reported. A variety of para-substituted phenols are amenable to this methodology, affording the desired products in moderate to good yields. Our protocol is expedient and practical and is carried out under microwave irradiation in only 3 min under air. A plausible catalytic cycle is proposed based on experimental mechanistic investigations and density functional theory (DFT) calculations. |
| doi_str_mv | 10.1021/acs.joc.3c00830 |
| format | Article |
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Org. Chem</addtitle><date>2023-08-18</date><risdate>2023</risdate><volume>88</volume><issue>16</issue><spage>11552</spage><epage>11561</epage><pages>11552-11561</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>Benzoxanthenes and their analogues are a very important class of compounds mainly due to their wide range of biological and technological applications. The development of a new methodology for their synthesis, involving an Ullmann-type coupling followed by an intramolecular C–H arylation, catalyzed by copper in a domino fashion, is reported. A variety of para-substituted phenols are amenable to this methodology, affording the desired products in moderate to good yields. Our protocol is expedient and practical and is carried out under microwave irradiation in only 3 min under air. 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| language | eng |
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| source | American Chemical Society Journals |
| subjects | air arylation copper density functional theory microwave radiation microwave treatment organic chemistry |
| title | Microwave-Assisted, Copper-Catalyzed Domino O–H/C–H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules |
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