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金属卟啉类染料催化的卡宾转移反应。

Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group.

机构信息

Department of Chemistry & Organic Chemistry, Natural Products and Food Stuffs Unit (QOPNA), University of Aveiro, 3810-193 Aveiro, Portugal.

Departamento de Química Orgânica, Universidade Federal Fluminense, Niterói 24020-150, RJ, Brazil.

出版信息

Molecules. 2018 Mar 29;23(4):792. doi: 10.3390/molecules23040792.

DOI:10.3390/molecules23040792
PMID:29596367
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6017490/
Abstract

Carbene transfer reactions are very important transformations in organic synthesis, allowing the generation of structurally challenging products by catalysed cyclopropanation, cyclopropenation, carbene C-H, N-H, O-H, S-H, and Si-H insertion, and olefination of carbonyl compounds. In particular, chiral and achiral metalloporphyrins have been successfully explored as biomimetic catalysts for these carbene transfer reactions under both homogeneous and heterogeneous conditions. In this work the use of synthetic metalloporphyrins (MPorph, M = Fe, Ru, Os, Co, Rh, Ir, Sn) as homogeneous or heterogeneous catalysts for carbene transfer reactions in the last years is reviewed, almost exclusively focused on the literature since the year 2010, except when reference to older publications was deemed to be crucial.

摘要

卡宾转移反应在有机合成中非常重要,通过催化的环丙烷化、环丙烯化、卡宾 C-H、N-H、O-H、S-H 和 Si-H 插入以及羰基化合物的烯化反应,可以生成具有挑战性的结构产物。特别是,手性和非手性金属卟啉已被成功探索作为这些卡宾转移反应的仿生催化剂,在均相和多相条件下均有应用。在这项工作中,综述了近年来使用合成金属卟啉(MPorph,M = Fe、Ru、Os、Co、Rh、Ir、Sn)作为均相或多相催化剂进行卡宾转移反应的情况,几乎完全集中在 2010 年以后的文献上,除非认为参考较早的出版物至关重要。

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Inorg Chem. 2021 Dec 20;60(24):18575-18588. doi: 10.1021/acs.inorgchem.1c01860. Epub 2021 Aug 25.
5
An In-Depth Computational Study of Alkene Cyclopropanation Catalyzed by Fe(porphyrin)(OCH) Complexes. The Environmental Effects on the Energy Barriers.铁(卟啉)(OCH)配合物催化烯烃环丙烷化的深入计算研究。环境对能垒的影响。
Inorg Chem. 2020 Aug 17;59(16):11329-11336. doi: 10.1021/acs.inorgchem.0c00912. Epub 2020 Jul 26.
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Recent Advances in Catalyzed Sequential Reactions and the Potential Use of Tetrapyrrolic Macrocycles as Catalysts.最近在催化串联反应方面的进展和四吡咯大环作为催化剂的潜在应用。
Molecules. 2018 Oct 28;23(11):2796. doi: 10.3390/molecules23112796.
铁原卟啉肌红蛋白催化的环丙烷化反应:由于卡宾物种的快速形成而加速催化。
J Am Chem Soc. 2017 Dec 6;139(48):17265-17268. doi: 10.1021/jacs.7b10154. Epub 2017 Nov 22.
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Molecular catalysis at polarized interfaces created by ferroelectric BaTiO.由铁电体钛酸钡产生的极化界面处的分子催化作用
Chem Sci. 2017 Apr 1;8(4):2790-2794. doi: 10.1039/c6sc05032h. Epub 2017 Feb 6.
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Hemin-catalyzed sulfonium ylide formation and subsequently reactant-controlled chemoselective rearrangements.氯化血红素催化硫叶立德的形成以及随后反应物控制的化学选择性重排。
Chem Commun (Camb). 2017 Jun 6;53(46):6219-6222. doi: 10.1039/c7cc02484c.
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Beyond Iron: Iridium-Containing P450 Enzymes for Selective Cyclopropanations of Structurally Diverse Alkenes.超越铁元素:含铱的细胞色素P450酶用于结构多样烯烃的选择性环丙烷化反应
ACS Cent Sci. 2017 Apr 26;3(4):302-308. doi: 10.1021/acscentsci.6b00391. Epub 2017 Apr 1.
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Cyclopropanation Strategies in Recent Total Syntheses.近期全合成中涉及的环丙烷化策略。
Chem Rev. 2017 Sep 27;117(18):11651-11679. doi: 10.1021/acs.chemrev.6b00798. Epub 2017 May 3.
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Engineering catalytic coordination space in a chemically stable Ir-porphyrin MOF with a confinement effect inverting conventional Si-H insertion chemoselectivity.在具有限域效应的化学稳定铱卟啉金属有机框架中构建催化配位空间,该限域效应使传统的硅氢插入化学选择性发生反转。
Chem Sci. 2017 Jan 1;8(1):775-780. doi: 10.1039/c6sc03288e. Epub 2016 Sep 1.
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Engineering of RuMb: Toward a Green Catalyst for Carbene Insertion Reactions.RuMb的工程设计:迈向用于卡宾插入反应的绿色催化剂
Inorg Chem. 2017 May 15;56(10):5623-5635. doi: 10.1021/acs.inorgchem.6b03148. Epub 2017 Apr 26.
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Highly Diastereo- and Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes via Myoglobin-Catalyzed Transfer of Trifluoromethylcarbene.过氧化物酶体增殖物激活受体γ共激活因子 1α 在糖代谢和胰岛素信号转导中的作用
J Am Chem Soc. 2017 Apr 19;139(15):5293-5296. doi: 10.1021/jacs.7b00768. Epub 2017 Apr 10.