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无过渡金属的苄基C(sp) -H活化/官能团化反应的进展与发展

Advances and developments in transition metal-free benzylic C(sp)-H activation/functionalization reactions.

作者信息

Doraghi Fatemeh, Kermaninia Shahab, Ghalehsefid Elika Salehi, Larijani Bagher, Mahdavi Mohammad

机构信息

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences Tehran Iran

School of Chemistry, College of Science, University of Tehran Tehran Iran.

出版信息

RSC Adv. 2025 May 7;15(19):14691-14716. doi: 10.1039/d5ra00361j. eCollection 2025 May 6.

DOI:10.1039/d5ra00361j
PMID:40337228
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12056733/
Abstract

Transition metal-free C(sp)-H activation of toluene derivatives is known as a green and sustainable methodology for constructing carbon-carbon and carbon-heteroatom bonds. Benzylic C(sp)-H activation/functionalization bond formation can be carried out in the presence of organic/inorganic peroxides, bases, acids, and other radical initiators. These radical transformations also occur under photochemical and electrochemical conditions. In this review, we highlight the C-H activation/annulation or C-H activation/functionalization reactions of benzylic carbon atoms in the presence of non-metal catalysts or promoters or without any catalyst.

摘要

甲苯衍生物的无过渡金属C(sp)-H活化是构建碳-碳和碳-杂原子键的一种绿色且可持续的方法。苄基C(sp)-H活化/官能化键的形成可以在有机/无机过氧化物、碱、酸和其他自由基引发剂存在的情况下进行。这些自由基转化也能在光化学和电化学条件下发生。在本综述中，我们重点介绍了在无金属催化剂或促进剂存在下或无任何催化剂时苄基碳原子的C-H活化/环化或C-H活化/官能化反应。

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Direct functionalization of M-C (M = Pt(II), Pd(II)) bonds using environmentally benign oxidants, O2 and H2O2.使用环境友好型氧化剂 O2 和 H2O2 直接官能化 M-C（M = Pt(II), Pd(II)）键。
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Synthesis of Indolines via Base-Mediated C-H Activation and Defluorinative C-N Coupling, with no Need for Transition-Metals.通过碱介导的C-H活化和脱氟C-N偶联合成二氢吲哚，无需过渡金属。
Chemistry. 2024 Jul 2;30(37):e202401034. doi: 10.1002/chem.202401034. Epub 2024 May 27.
2
Electrochemical Benzylic C(sp)-H Imidation Enabled by Benzoic Acid Derived Radicals.由苯甲酸衍生自由基实现的电化学苄基C(sp)-H亚胺化反应
J Org Chem. 2024 May 3;89(9):6395-6404. doi: 10.1021/acs.joc.4c00425. Epub 2024 Apr 15.
3
Cross-Coupling of Benzylic and Aldehydic C-H Bonds via Photocatalytic Tandem Radical-Radical Coupling and Acceptorless Alcohol Dehydrogenation.
通过光催化串联自由基-自由基偶联和无受体醇脱氢实现苄基和醛基C-H键的交叉偶联
J Org Chem. 2024 Feb 2;89(3):2032-2038. doi: 10.1021/acs.joc.3c02427. Epub 2024 Jan 16.
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Olefin Difunctionalization for the Synthesis of Tetrahydroisoquinoline, Morpholine, Piperazine, and Azepane.用于合成四氢异喹啉、吗啉、哌嗪和氮杂环庚烷的烯烃双官能团化反应
Org Lett. 2024 Jan 12;26(1):84-88. doi: 10.1021/acs.orglett.3c03690. Epub 2024 Jan 3.
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Metal-free photoinduced C(sp)-H/C(sp)-H cross-coupling to access α‑tertiary amino acid derivatives.通过无金属光诱导C(sp)-H/C(sp)-H交叉偶联反应合成α-叔氨基酸衍生物。
Nat Commun. 2023 Oct 6;14(1):6225. doi: 10.1038/s41467-023-41956-6.
6
Switchable Direct Oxygenative Arylation of C(sp)-H Bonds via Electrophotocatalysis.通过电光催化实现 C(sp(2))-H 键的可切换直接氧化芳基化反应。
Org Lett. 2023 Jul 14;25(27):5067-5072. doi: 10.1021/acs.orglett.3c01751. Epub 2023 Jun 30.
7
Organopotassium-Catalyzed Silylation of Benzylic C(sp )-H Bonds.有机钾催化苄基C(sp³)-H键的硅基化反应
Angew Chem Int Ed Engl. 2023 Aug 1;62(31):e202306115. doi: 10.1002/anie.202306115. Epub 2023 Jun 26.
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Visible-Light-Driven Organocatalytic Alkoxylation of Benzylic C-H Bonds.可见光促进的苄位 C-H 键的有机催化烷氧基化反应。
J Org Chem. 2023 Mar 17;88(6):3532-3538. doi: 10.1021/acs.joc.2c02743. Epub 2023 Mar 7.
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Direct Benzylic C-H Functionalization with Fluorenones under Visible-Light Irradiation.在可见光照射下，利用芴酮直接进行苄位 C-H 官能化。
J Org Chem. 2023 Feb 17;88(4):2612-2620. doi: 10.1021/acs.joc.2c02766. Epub 2023 Feb 1.
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Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp)-H bonds.碘（III）促进N-羟基邻苯二甲酰亚胺与未活化的C(sp)-H键的交叉脱氢偶联反应。
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