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镍电催化室温下温和的C-H烷基化反应

Nickela-electrocatalyzed Mild C-H Alkylations at Room Temperature.

作者信息

Samanta Ramesh C, Struwe Julia, Ackermann Lutz

机构信息

Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077, Göttingen, Germany.

Woehler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, Tammannstrasse 2, 37077, Göttingen, Germany.

出版信息

Angew Chem Int Ed Engl. 2020 Aug 10;59(33):14154-14159. doi: 10.1002/anie.202004958. Epub 2020 Jun 8.

DOI:10.1002/anie.202004958
PMID:32324948
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7496282/
Abstract

Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures and strong bases, translating into limited substrate scope. Herein, nickel-catalyzed C-H alkylations of unactivated 8-aminoquinoline amides have been realized under exceedingly mild conditions, namely at room temperature, with a mild base and a user-friendly electrochemical setup. This electrocatalyzed C-H alkylation displays high functional group tolerance and is applicable to both the primary and secondary alkylation. Based on detailed mechanistic studies, a nickel(II/III/I) catalytic manifold has been proposed.

摘要

羧酸衍生物的直接烷基化具有挑战性，特别是镍催化通常需要高反应温度和强碱，这导致底物范围有限。在此，未活化的8-氨基喹啉酰胺的镍催化C-H烷基化已在极其温和的条件下实现，即在室温下，使用温和的碱和用户友好的电化学装置。这种电催化的C-H烷基化表现出高官能团耐受性，适用于一级和二级烷基化。基于详细的机理研究，提出了镍（II/III/I）催化机理。

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2
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Chem Sci. 2019 Aug 19;10(41):9493-9500. doi: 10.1039/c9sc01446b. eCollection 2019 Nov 7.
3
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4
A facile method for Rh-catalyzed decarbonylative -C-H alkylation of (hetero)arenes with alkyl carboxylic acids.一种用于铑催化（杂）芳烃与烷基羧酸进行脱羰基-C-H烷基化反应的简便方法。
RSC Adv. 2021 Jun 2;11(32):19827-19831. doi: 10.1039/d1ra03992j. eCollection 2021 May 27.
5
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6
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