Mechanism of Photoredox-Initiated C–C and C–N Bond Formation by Arylation of IPrAu(I)–CF3 and IPrAu(I)–Succinimide
Herein, we report on the photoredox-initiated gold-mediated C(sp2)–CF3 and C(sp2)–N coupling reactions. By adopting gold as a platform for probing metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of the C–C and C–N coupling reactions. The hig...
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| Published in | Journal of the American Chemical Society Vol. 141; no. 10; pp. 4308 - 4315 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
American Chemical Society
13.03.2019
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| Online Access | Get full text |
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| Summary: | Herein, we report on the photoredox-initiated gold-mediated C(sp2)–CF3 and C(sp2)–N coupling reactions. By adopting gold as a platform for probing metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of the C–C and C–N coupling reactions. The high-valent gold(III) intermediates are accessed by virtue of photoredox catalysis through a radical chain process. In addition, the bond-forming step of the coupling reactions is the reductive elimination from cationic gold(III) intermediates, which is supported by isolation and crystallographic characterization of key Au(III) intermediates. |
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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 0002-7863 1520-5126 |
| DOI: | 10.1021/jacs.8b11273 |