Diazo- and Transition-Metal-Free C-H Insertion: A Direct Synthesis of beta-Lactams

Gomes Luis F. R.; Veiros Luis F.; Maulide Nuno; Afonso Carlos A. M.

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Diazo- and Transition-Metal-Free C-H Insertion: A Direct Synthesis of beta-Lactams

机译：重氮和无过渡金属的C-H插入：β-内酰胺的直接合成

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Carbene intermediates are very useful species for a range of reactions including C-H insertions and cycloadditions. They are most commonly generated by metal-catalyzed release of nitrogen gas from diazo precursors. Herein, we present a novel C-H insertion of simple b-ketoamide substrates, through reaction with (diacetoxyiodo) benzene (DIB) in the presence of a base. This unprecedented transformation bypasses the use of either diazo precursors or metal catalysts and directly delivers beta-lactam products by an iodonium ylide, in a single step under mild conditions. Mechanistic studies support the intermediacy of a free singlet carbene of unique reactivity and selectivity.

机译：碳氢化合物中间体对于包括C-H插入和环加成在内的一系列反应非常有用。它们最通常由重氮前体的金属催化释放氮气产生。在本文中，我们介绍了通过与（二乙酰氧基碘）苯（DIB）在碱存在下反应，将简单的B-酮酰胺底物进行新颖的C-H插入。这种空前的转化无需使用重氮前体或金属催化剂，而仅需一步即可在温和的条件下通过碘鎓叶立德直接提供β-内酰胺产品。机理研究支持具有独特反应性和选择性的游离单线卡宾的中间体。

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《Chemistry: A European journal》 |2015年第4期|共5页
作者
Gomes Luis F. R.; Veiros Luis F.; Maulide Nuno; Afonso Carlos A. M.;
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正文语种 eng
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carbenes; C-H insertion; iodonium ylides; lactams; reaction mechanism;

机译：卡宾;C-H插入;碘鎓;内酰胺;反应机理;

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1. Diazo- and Transition-Metal-Free C-H Insertion: A Direct Synthesis of beta-Lactams [J] . Gomes Luis F. R., Veiros Luis F., Maulide Nuno, Chemistry: A European journal . 2015,第4期

机译：重氮和无过渡金属的C-H插入：β-内酰胺的直接合成
2. Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent [J] . Amy E. Shiely, Catherine N. Slattery, Alan Ford, Organic & biomolecular chemistry . 2017,第12期

机译：对映选择性铜催化α-重氮-β-酮砜，α-重氮-β-酮膦氧化物和2-重氮-1,3-二酮的分子内C-H插入反应；卡宾取代基的影响
3. Copper-catalysed enantioselective intramolecular C-H insertion reactions of α-diazo-β-keto esters and α-diazo-β-keto phosphonates [J] . Catherine N. Slattery, Anita R. Maguire Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2013,第22期

机译：铜催化α-重氮-β-酮酸酯和α-重氮-β-酮酸酯的分子内C-H插入反应
4. Highly Efficient Synthesis of Oxindole Derivatives via Catalytic Intramolecular C-H Insertion Reactions of Diazoamides [C] . Nga Phan-Thi-Thanh, Masaya Tone, Hayato lnoue International Conference on Science and Technology . 2020

机译：通过催化分子内C-H插入式重氮酰胺的催化分子内C-H插入反应高效合成氧吲哚衍生物
5. STUDIES IN ORGANOSULFUR CHEMISTRY. I. NUCLEAR MAGNETIC RESONANCE (PROTON, CARBON-13, OXYGEN-17 (1) J(C-H)) INVESTIGATIONS OF ORGANOSULFUR COMPOUNDS. II. MECHANISTIC STUDY OF PHASE TRANSFER CATALYZED REACTIONS OF DICHLOROCARBENE WITH SULFIDES AND SULFOXIDES. III. STUDIES DIRECTED TOWARD ASYMMETRIC SYNTHESIS USING CHIRAL PHASE TRANSFER CATALYSTS. [D] . DYER, JOHN COLLINS. 1980

机译：有机硫化学研究。 I.有机硫化合物的核磁共振（质子，碳13，氧17（1）J（C-H））研究。二。二氯卡宾与硫化物和硫化物的相转移催化反应的机理研究。三，使用手性相转移催化剂进行不对称合成的研究。
6. Direct Prenylation of Aromatic and αβ-Unsaturated Carboxamides via Iridium Catalyzed C-H Oxidative Addition-Allene Insertion [O] . Yong Jian Zhang, Eduardas Skucas, Michael J. Krische -1

机译：通过铱催化的C-H氧化加成 - 丙二烯插入芳香和αβ不饱和羧酰胺的直接异戊二烯化
7. Back Cover: Diazo- and Transition-Metal-Free CH Insertion: A Direct Synthesis of β-Lactams (Chem. Eur. J. 4/2015) [O] . Luis F. R. Gomes, Luís F. Veiros, Nuno Maulide, 2015

机译：返回盖子：无分配和过渡 - 无金属Ch插入：直接合成β-内酰胺（Chem.Eur。J. 4/2015）
8. Synthesis of nido- and closo-diplatinacarborane Complexes by Direct Insertion; Crystal and Molecular Structures of closo-2-3-((Et3P)2)2-1-2-3-6-CPt2CB5H7-nido-4-8-((Me3P)2Pt)-8- 8((Me3P)2)-7-8-10-CPtCB8H10 and nido-8-8-((Me3P)2)-7-8-10-CPtCB8H10. [R] . Barker, G. K., Green, M., Spencer, J. L., 1975

机译：直接插入法合成nido-和closo-diplatinacarborane配合物; closo-2-3 - （（Et3p）2）2-1-2-3-6-Cpt2CB5H7-nido-4-8 - （（me3p）2pt）-8-8（（me3p）2的晶体和分子结构）-7-8-10-CptCB8H10和nido-8-8 - （（me3p）2）-7-8-10-CptCB8H10。

Diazo- and Transition-Metal-Free C-H Insertion: A Direct Synthesis of beta-Lactams

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