Recent Developments in Organoboron Chemistry: Old Dogs, New Tricks

Chem, Journal Year: 2017, Volume and Issue: 3(1), P. 31 - 55

Published: July 1, 2017

Language: Английский

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Cross-coupling of aromatic esters and amides

Chemical Society Reviews, Journal Year: 2017, Volume and Issue: 46(19), P. 5864 - 5888

Published: Jan. 1, 2017

This review highlights the progress in transition-metal-catalyzed decarbonylative and non-decarbonylative cross-coupling of aromatic esters amides.

Language: Английский

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Breaking Amides using Nickel Catalysis

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(2), P. 1413 - 1423

Published: Jan. 7, 2017

Amides have been widely studied for decades, but their synthetic utility has remained limited in reactions that proceed with rupture of the amide C-N bond. Using Ni catalysis, we found amides can now be strategically employed several important transformations: esterification, transamidation, Suzuki-Miyaura couplings, and Negishi couplings. These methodologies provide exciting new tools to build C-heteroatom C-C bonds using an unconventional reactant (i.e., amide), which is ideally suited use multi-step synthesis. It expected area bond activation nonprecious metals will continue flourish and, turn, promote growing as synthons organic

Language: Английский

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Well-defined nickel and palladium precatalysts for cross-coupling

Nature Reviews Chemistry, Journal Year: 2017, Volume and Issue: 1(3)

Published: March 1, 2017

Language: Английский

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Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future

Organometallics, Journal Year: 2018, Volume and Issue: 38(1), P. 3 - 35

Published: Nov. 27, 2018

Cross-coupling reactions, which were discovered almost 50 years ago, are widely used in both industry and academia. Even though cross-coupling reactions now represent mature technology, there is still a significant amount of research this area that aims to improve the scope these develop more efficient catalysts, make practical. In tutorial, brief background provided, then major advances over last 20 described. These include development improved ligands precatalysts for extension much wider range electrophiles. For example, common with sp3-hybridized electrophiles as well ester, amide, ether, aziridine substrates. many modern substrates, traditional palladium-based catalysts less than systems based on first-row transition metals such nickel. Conventional have also inspired related cross-electrophile decarboxylative couplings metallaphotoredox chemistry. The new probably at same stage 30 tutorial highlights how strategies may be applicable making

Language: Английский

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Amide activation: an emerging tool for chemoselective synthesis

Chemical Society Reviews, Journal Year: 2018, Volume and Issue: 47(21), P. 7899 - 7925

Published: Jan. 1, 2018

This review focusses on the use of amide activation for chemoselective functionalisation and its application in natural product synthesis.

Language: Английский

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Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C–N Bond Activation

Journal of the American Chemical Society, Journal Year: 2017, Volume and Issue: 139(15), P. 5313 - 5316

Published: March 31, 2017

We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example metal-catalyzed activation an amine with unactivated group. reaction enjoys broad scope and functional group tolerance. Primary secondary groups can be installed. Preliminary studies suggest Ni

Language: Английский

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Twisted Amides: From Obscurity to Broadly Useful Transition‐Metal‐Catalyzed Reactions by N−C Amide Bond Activation

Chemistry - A European Journal, Journal Year: 2016, Volume and Issue: 23(30), P. 7157 - 7173

Published: Nov. 4, 2016

Abstract The concept of using amide bond distortion to modulate amidic resonance has been known for more than 75 years. Two classic twisted amides (bridged lactams) ingeniously designed and synthesized by Kirby Stoltz feature fully perpendicular bonds, as a consequence emanate amino‐ketone‐like reactivity, are now routinely recognized in all organic chemistry textbooks. However, only recently the use twist (distortion) advanced general mainstream enabling host highly attractive N−C cross‐coupling reactions broad synthetic relevance. In this Minireview, we discuss recent progress area present detailed overview prominent role destabilization driving force development transition‐metal‐catalyzed activation.

Language: Английский

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Base-free nickel-catalysed decarbonylative Suzuki–Miyaura coupling of acid fluorides

Nature, Journal Year: 2018, Volume and Issue: 563(7729), P. 100 - 104

Published: Oct. 23, 2018

Language: Английский

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Palladium-Catalyzed Suzuki–Miyaura Coupling of Aryl Esters

Journal of the American Chemical Society, Journal Year: 2016, Volume and Issue: 139(3), P. 1311 - 1318

Published: Dec. 21, 2016

The Suzuki–Miyaura coupling is among the most important C–C bond-forming reactions available due to its reliability, chemoselectivity, and diversity. Aryl halides pseudohalides such as iodides, bromides, triflates are traditionally used electrophilic partner. expansion of reaction scope nontraditional electrophiles an ongoing challenge enable even greater number useful products be made from simple starting materials. Herein, we present how NHC-based Pd catalyst can where C(acyl)–O bond aryl esters takes on role electrophile, allowing synthesis various ketone-containing products. This contrasts known similar that provide biaryls via nickel catalysis. underlying cause this mechanistic divergence investigated by DFT calculations, robustness compared more acylative partners analyzed.

Language: Английский

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