Catalytic C–H functionalization by metalloporphyrins: recent developments and future directions

Lü, Hongjian; Zhang, X. Peter

doi:10.1039/c0cs00070a

Cited by 647 publications

(301 citation statements)

References 38 publications

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“…The vast metalloporphyrin catalysis literature (e.g. Lu & Zhang, 2011) provides a rich source of inspiration and ideas for future work. Fig.…”

Section: Discussionmentioning

confidence: 99%

The nature of chemical innovation: new enzymes by evolution

Arnold

2015

Quart. Rev. Biophys.

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Abstract. I describe how we direct the evolution of non-natural enzyme activities, using chemical intuition and information on structure and mechanism to guide us to the most promising reaction/enzyme systems. With synthetic reagents to generate new reactive intermediates and just a few amino acid substitutions to tune the active site, a cytochrome P450 can catalyze a variety of carbene and nitrene transfer reactions. The cyclopropanation, N-H insertion, C-H amination, sulfimidation, and aziridination reactions now demonstrated are all well known in chemical catalysis but have no counterparts in nature. The new enzymes are fully genetically encoded, assemble and function inside of cells, and can be optimized for different substrates, activities, and selectivities. We are learning how to use nature's innovation mechanisms to marry some of the synthetic chemists' favorite transformations with the exquisite selectivity and tunability of enzymes.

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“…The vast metalloporphyrin catalysis literature (e.g. Lu & Zhang, 2011) provides a rich source of inspiration and ideas for future work. Fig.…”

Section: Discussionmentioning

confidence: 99%

The nature of chemical innovation: new enzymes by evolution

Arnold

2015

Quart. Rev. Biophys.

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“…This second part focuses on asymmetric catalysis using metalloporphyrins (metals: Fe, Ru, Mn) as catalysts conducted by our group. There are excellent and recent reviews devoted to this topic [29,30].…”

Section: Enantioselective Catalysismentioning

confidence: 99%

Metalloporphyrin Symmetry in Chiral Recognition and Enantioselective Catalysis

et al. 2014

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Symmetry plays a fundamental role in chiral recognition and enantioselective catalysis. Porphyrins possess a number of structural features that make them attractive for the stereocontrol of chiral recognition and metal-catalyzed asymmetric reactions. This article is a brief account of our studies on chiral recognition and enantioselective catalysis by optically active metalloporphyrins. Some of the studies on chiral recognition and asymmetric catalysis by metalloporphyrins performed by others have also been included when useful.

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“…As a result these molecules and their derivatives have long attracted the interest of biologists and biochemists. [1,2] Porphyrins have good thermal stability and versatile chemical properties, making them candidates for a wide variety of applications such as catalysis, [3,4] solar energy conversion, [5,6] and the development of metal-organic frameworks. [7][8][9] Among the porphyrins, 5,10,15,20-Tetra(4-pyridyl)porphyrin (H2TPyP) is one of the meso-substituted prophyrins that have been widely used in various chemical and photochemical studies.…”

Section: Introductionmentioning

confidence: 99%

“…Helium nanodroplets are large helium clusters composed of typically 10 3 -10 8 helium atoms. [18,19] These droplets have an equilibrium temperature of 0.37 K (for 4 He) and they can pick up atoms/molecules with a near unit probability. [20] When different types of atoms/molecules are added to the droplets, aggregation into binary complexes is expected.…”

Section: Introductionmentioning

confidence: 99%

Formation of Au and tetrapyridyl porphyrin complexes in superfluid helium

Cheng

Latimer

Spence

et al. 2015

Phys. Chem. Chem. Phys.

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Binary clusters containing a large organic molecule and metal atoms have been formed by the co-addition of 5,10,15,20-Tetra(4-pyridyl)porphyrin (H2TPyP) molecules and gold atoms to superfluid helium nanodroplets, and the resulting complexes were then investigated by electron impact mass spectrometry. In addition to the parent ion H2TPyP yields fragments mainly from pyrrole, pyridine and methylpyridine ions because of the stability of their ring structures. When Au is co-added to the droplets the mass spectra are dominated by H2TPyP fragment ions with one or more Au atoms attached. We also show that by switching the order in which Au and H2TPyP are added to the helium droplets, different types of H2TPyP/Au complexes are clearly evident from the mass spectra. This study suggests a new route for the control over the growth of metal-organic compounds inside superfluid helium nanodroplets.3

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Catalytic C–H functionalization by metalloporphyrins: recent developments and future directions

Cited by 647 publications

References 38 publications

The nature of chemical innovation: new enzymes by evolution

The nature of chemical innovation: new enzymes by evolution

Metalloporphyrin Symmetry in Chiral Recognition and Enantioselective Catalysis

Formation of Au and tetrapyridyl porphyrin complexes in superfluid helium

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