A New Procedure for the Oxidation of Saturated Hydrocarbons

BARTON, D. H. R.; Gastiger, Mj; Motherwell, W. B.

doi:10.1142/9789812795984_0125

Cited by 2 publications

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“…110 In the Gif oxygenation systems, these ferryl species are formed directly from O 2 in the presence of reductants (Zn or NaS) and pyridine. [111][112][113] While the culmination of this body of work has indeed yielded catalytic systems that can functionalize strong C-H bonds, many of these fundamentally important reactions suffer from unproductive oxidation and precipitation of the catalyst, a general lack of control over intermediary radical species, and limited regio-and stereoselectivity, hindering their applications more broadly.…”

Section: Reactions Of Ferrous Iron With Oxygen Speciesmentioning

confidence: 99%

Nature’s Machinery, Repurposed: Expanding the Repertoire of Iron-Dependent Oxygenases

2020

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Iron is an especially important redox-active cofactor in biology because of its ability to mediate reactions with atmospheric O 2 . Iron-dependent oxygenases exploit this earthabundant transition metal for the insertion of oxygen atoms into organic compounds. Throughout the astounding diversity of transformations catalyzed by these enzymes, the protein framework directs reactive intermediates toward the precise formation of products, which, in many cases, necessitates the cleavage of strong C-H bonds. In recent years, members of several iron-dependent oxygenase families have been engineered for new-to-nature transformations that offer advantages over conventional synthetic methods. In this Perspective, we first explore what is known about the reactivity of heme-dependent cytochrome P450 oxygenases and nonheme iron-dependent oxygenases bearing the 2-His-1-carboxylate facial triad by reviewing mechanistic studies with an emphasis on how the protein scaffold maximizes the catalytic potential of the iron-heme and iron cofactors. We then review how these cofactors have been repurposed for abiological transformations by engineering the protein frameworks of these enzymes. Finally, we discuss contemporary challenges associated with engineering these platforms and comment on their roles in biocatalysis moving forward.

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Section: Reactions Of Ferrous Iron With Oxygen Speciesmentioning

confidence: 99%

Nature’s Machinery, Repurposed: Expanding the Repertoire of Iron-Dependent Oxygenases

2020

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“…Pre-eminent in this field is Nobel Laureate Derek Barton's work, which has become known as Gif and GoAgg chemistry (named after their sites of discovery: Gif-sur-Yvette, France and Texas A&M, respectively). The first generation of Gif chemistry, initially disclosed in 1983, 486 used iron powder, sodium sulfide, acetic acid, and oxygen to oxidize adamantane with pyridine as solvent. The mechanism of Gif oxidation of adamantane has been the subject of much study.…”

Section: Biomimetic C−h Oxidationmentioning

confidence: 99%

Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis

2017

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First-row transition-metal-mediated reactions constitute an important and growing area of research due to the low cost, low toxicity, and exceptional synthetic versatility of these metals. Currently, there is considerable effort to replace existing precious-metal-catalyzed reactions with first-row analogs. More importantly, there are a plethora of unique transformations mediated by first-row metals, which have no classical second- or third-row counterpart. Herein, the application of first-row metal-mediated methods to the total synthesis of natural products is discussed. This Review is intended to highlight strategic uses of these metals to realize efficient syntheses and highlight the future potential of these reagents and catalysts in organic synthesis.

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A New Procedure for the Oxidation of Saturated Hydrocarbons

Cited by 2 publications

References 0 publications

Nature’s Machinery, Repurposed: Expanding the Repertoire of Iron-Dependent Oxygenases

Nature’s Machinery, Repurposed: Expanding the Repertoire of Iron-Dependent Oxygenases

Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis

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