Sustainable electrochemical dehydrogenative C(sp)-H mono/di-alkylations

Catalyst-free, direct electrooxidative phenol derivatives C(sp 3 )-H mono- and di-alkylation reaction have been developed. In contrast to previous typical oxidative and electrochemical coupling, this electrosynthetic approach enables selective mono- and di-alkylations through metal- and external oxi...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2022-03, Vol.24 (6), p.2483-2491
Hauptverfasser: He, Jin-Yu, Qian, Wei-Feng, Wang, Yan-Zhao, Yao, Chaochao, Wang, Nana, Liu, Huilin, Zhong, Bing, Zhu, Cuiju, Xu, Hao
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Sprache:eng
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Zusammenfassung:Catalyst-free, direct electrooxidative phenol derivatives C(sp 3 )-H mono- and di-alkylation reaction have been developed. In contrast to previous typical oxidative and electrochemical coupling, this electrosynthetic approach enables selective mono- and di-alkylations through metal- and external oxidant-free mild conditions via easily available electrodes. Advances of this strategy were proven by an unparalleled broad substrate scope for efficient C-C, C-N, C-O bond formation as well as excellent site- and regioselectivity. The electrochemical selective alkylations were devoid of additional electrolytes, could be conducted on a gram scale, and provided the enone products by cascade electrooxidative dehydrogenation, which highlight a notable potential for further late-stage diversification. Detailed mechanistic studies allowed to delineate the exact profile of the generation of the mono- and di-alkylation events. Catalyst-free, direct electrooxidative phenol derivatives C(sp 3 )-H mono- and di-alkylation reaction have been developed.
ISSN:1463-9262
1463-9270
DOI:10.1039/d1gc04479f