Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX 2
We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible fo...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2021-10, Vol.60 (42), p.22977-22982 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Dhungana, Roshan K Sapkota, Rishi R Wickham, Laura M Niroula, Doleshwar Shrestha, Bijay Giri, Ramesh |
| description | We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate-limiting single-electron-transfer process and is autocatalyzed by in-situ-generated ZnX
. The reaction rate is amplified by a factor of three through autocatalysis upon addition of ZnX
. |
| doi_str_mv | 10.1002/anie.202110459 |
| format | Article |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Alkenes - chemistry Benzyl Compounds - chemistry Bromides - chemistry Catalysis Kinetics Nickel - chemistry Zinc Compounds - chemistry |
| title | Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX 2 |
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