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Iron Porphyrin Catalyzed N−H Insertion Reactions with Ethyl Diazoacetate

Lynnette K. Baumann, +3 more
- 04 Jul 2007 - 
- Vol. 26, Iss: 16, pp 3995-4002
TLDR
In this article, a series of metalloporphyrin complexes were surveyed as catalysts for carbene insertion from ethyl diazoacetate into the N−H bonds of amines.
About
This article is published in Organometallics.The article was published on 2007-07-04 and is currently open access. It has received 98 citations till now. The article focuses on the topics: Ethyl diazoacetate & Insertion reaction.

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Citations
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Journal ArticleDOI

Modern Organic Synthesis with α-Diazocarbonyl Compounds

TL;DR: This work aims to demonstrate the efforts towards in-situ applicability of EMMARM, which aims to provide real-time information about the physical properties of EMTs and their applications in the context of drug discovery and development.
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Catalytic X–H insertion reactions based on carbenoids

TL;DR: The following review will explore the historical development of X-H insertion and give an up-to-date account of the metal catalysts most often employed, including an assessment of their strengths and weaknesses.
Journal ArticleDOI

Cytochrome P450-catalyzed insertion of carbenoids into N–H bonds

TL;DR: This work demonstrates enzyme-catalyzed insertion of carbenoids into N-H bonds, which has no counterpart in nature, and can be mediated by variants of the cytochrome P450 from Bacillus megaterium.
Journal ArticleDOI

Organic synthesis with the most abundant transition metal–iron: from rust to multitasking catalysts

TL;DR: The field of iron catalysis has been explored in the last two-three decades out of its rich chemistry depending on its oxidation states and ligand cooperation as discussed by the authors, and this field has been enriched by the promising development of iron-catalyzed reactions namely, C-H bond activation, including organometallic C−H activation and C−h functionalization via outer-sphere pathway, crossdehydrogenative couplings, insertion reactions, cross-coupling reactions, hydrogenations including hydrogen borrowing reactions, hydrosilylation and hydroboration, addition reactions
References
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Journal ArticleDOI

Iron(III) and ruthenium(II) porphyrin complex-catalyzed selective olefination of aldehydes with ethyl diazoacetate.

TL;DR: The reactions were carried out under mild conditions in a one-pot fashion with the use of a stoichiometrical amount of EDA, which proceeded with excellent yields and high (E)-selectivity.
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A New and Efficient Method for the Selective Olefination of Aldehydes with Ethyl Diazoacetate Catalyzed by an Iron(II) Porphyrin Complex

TL;DR: Olefination of aromatic and aliphatic aldehydes with ethyl diazoacetate was achieved in excellent yields with triphenylphosphine and catalytic amounts of iron(II) meso-tetra(p-tolyl)porphyrin.
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Organic Reactions Catalyzed by Methylrhenium Trioxide: Reactions of Ethyl Diazoacetate and Organic Azides

TL;DR: In this paper, the first high valent oxo complex for carbene transfer was converted to a 9:1 mixture of diethyl maleate (DHM) and fumarate.
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Cyclopropanation of Alkenes, N–H and S–H Insertion of Ethyl Diazoacetate Catalysed by Ruthenium Porphyrin Complexes

TL;DR: In this article, the product yields, stereoselectivities and regioselectivity for cyclopropanation reactions of ethyl diazoacetate with styrene derivatives and α-heteroatom alkenes, catalysed by ruthenium porphyrins, are reported and compared with observed stereosynthetic reactions catalysed with other metalloporphyrin catalysts.
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Catalytic Cyclopropanation with Iron(II) Complexes

TL;DR: In this article, the stereoselectivity of iron(II) porphyrin-catalyzed cyclopropanation reactions was enhanced by performing the reactions at low temperature or by using bulky porphrin ligands.
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