C–H nitrogenation and oxygenation by ruthenium catalysis

Chemical Communications, Journal Year: 2013, Volume and Issue: 50(1), P. 29 - 39

Published: Oct. 25, 2013

Remarkable recent progress has been accomplished in direct C-H functionalizations for the formation of C-N and C-O bonds through use readily accessible ruthenium catalysts. Particularly, ruthenium(II) complexes allowed challenging C(sp(2))-H hydroxylation arenes. These catalysts set stage step-economical functionalization with electron-rich as well electron-deficient (hetero)arenes and, therefore, provided versatile access to diversely decorated phenols. While a number synthetically useful protocols ruthenium-catalyzed C(sp(3))-H bond nitrogenation have elaborated, analogous transformations more stable were very recently achieved.

Language: Английский

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The Suzuki-Miyaura reaction after the Nobel prize

Coordination Chemistry Reviews, Journal Year: 2019, Volume and Issue: 385, P. 137 - 173

Published: Feb. 13, 2019

Language: Английский

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Understanding active species in catalytic transformations: From molecular catalysis to nanoparticles, leaching, “Cocktails” of catalysts and dynamic systems

Coordination Chemistry Reviews, Journal Year: 2017, Volume and Issue: 346, P. 2 - 19

Published: Jan. 7, 2017

Language: Английский

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Reactions of the 21st Century: Two Decades of Innovative Catalyst Design for Palladium-Catalyzed Cross-Couplings

Organometallics, Journal Year: 2015, Volume and Issue: 34(23), P. 5497 - 5508

Published: Oct. 16, 2015

A brief account of the major developments palladium-catalyzed cross-coupling during last two decades is highlighted chronologically, with an emphasis on personal experiences corresponding author. Important contributions from both academia and industry, which have been vital to accelerated growth this area, are presented. The new classes ligands switch in situ preformed catalysts tailored address challenges reviewed, reflecting evolution continued growth.

Language: Английский

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Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

Coordination Chemistry Reviews, Journal Year: 2019, Volume and Issue: 399, P. 213024 - 213024

Published: Sept. 5, 2019

Language: Английский

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The Evolution of Chemical High-Throughput Experimentation To Address Challenging Problems in Pharmaceutical Synthesis

Accounts of Chemical Research, Journal Year: 2017, Volume and Issue: 50(12), P. 2976 - 2985

Published: Nov. 27, 2017

ConspectusThe structural complexity of pharmaceuticals presents a significant challenge to modern catalysis. Many published methods that work well on simple substrates often fail when attempts are made apply them complex drug intermediates. The use high-throughput experimentation (HTE) techniques offers means overcome this fundamental by facilitating the rational exploration large arrays catalysts and reaction conditions in time- material-efficient manner. Initial forays into HTE our laboratories for solving chemistry problems centered around screening chiral precious-metal homogeneous asymmetric hydrogenation. success these early efforts developing efficient catalytic steps late-stage development programs motivated desire increase scope approach encompass other high-value chemistries. Doing so, however, required advances reactor workflow design automation enable effective assembly agitation heterogeneous mixtures retention volatile solvents under wide range temperatures. Associated innovations analytical greatly increased efficiency reliability methods. These evolved have been utilized extensively develop highly innovative catalysis solutions most challenging large-scale pharmaceutical synthesis. Starting with Pd- Cu-catalyzed cross-coupling chemistry, subsequent expanded valuable synthetic transformations such as phase-transfer catalysis, photoredox C–H functionalization. As experience confidence matured, we envisioned their application beyond process address needs medicinal chemists. Here problem generality is felt acutely, approaches should prove broadly enabling. However, quantities both time starting materials available troubleshooting space generally severely limited. Adapting led us invest smaller predefined transformation-specific “kits” push boundaries miniaturization screening, culminating “nanoscale” carried out 1536-well plates. Grappling also inspired cheminformatics-driven Chemistry Informer Libraries. next-generation promise empower chemists run orders magnitude more experiments “big data” informatics troubleshooting. With advances, poised revolutionize how across industry academia discover new methods, tools broad utility, practical significance.

Language: Английский

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The 25th Anniversary of the Buchwald–Hartwig Amination: Development, Applications, and Outlook

Organic Process Research & Development, Journal Year: 2019, Volume and Issue: 23(8), P. 1478 - 1483

Published: July 2, 2019

The palladium-catalyzed cross-coupling of amines and aryl (pseudo)halides, now commonly known as the Buchwald–Hartwig amination, was first reported 25 years ago. Since simultaneous breakthrough reports Buchwald Hartwig in 1995, this reaction has transformed way synthetic chemists think about synthesizing aromatic amines. In highlight article, a short showcasing discussion genesis is provided, along with selected examples showing impact transformation chemistry both academic industrial settings.

Language: Английский

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Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides

Journal of the American Chemical Society, Journal Year: 2014, Volume and Issue: 136(40), P. 14027 - 14030

Published: Sept. 23, 2014

We report the development of a Pd-catalyzed process for stereospecific cross-coupling unactivated secondary alkylboron nucleophiles and aryl chlorides. This tolerates use alkylboronic acids alkyltrifluoroborates occurs without significant isomerization alkyl nucelophile. Optically active alkyltrifluoroborate reagents undergo reactions with inversion configuration using this method.

Language: Английский

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Mechanistic Analysis of Metallaphotoredox C–N Coupling: Photocatalysis Initiates and Perpetuates Ni(I)/Ni(III) Coupling Activity

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(37), P. 15830 - 15841

Published: Aug. 4, 2020

The combined use of reaction kinetic analysis, ultrafast spectroscopy, and stoichiometric organometallic studies has enabled the elucidation mechanistic underpinnings to a photocatalytic C-N cross-coupling reaction. Steady-state spectroscopic techniques were used track excited-state evolution employed iridium photocatalyst, determine resting states both nickel catalysts, uncover photochemical mechanism for reductive activation cocatalyst. Stoichiometric along with comprehensive study reaction, including rate-driving force unveiled crucial role photocatalysis in initiating sustaining Ni(I)/Ni(III) mechanism. insights gleaned from this further discovery new photocatalyst providing >30-fold rate increase.

Language: Английский

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Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

Chemical Science, Journal Year: 2016, Volume and Issue: 7(4), P. 2604 - 2613

Published: Jan. 1, 2016

We report a standardized complex molecule diagnostic approach using collections of relevant drug-like molecules which we call chemistry informer libraries.

Language: Английский

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