Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by in Situ Crystallization DOI

Tamae Seo,

Koji Kubota, Hajime Ito

и другие.

Journal of the American Chemical Society, Год журнала: 2020, Номер 142(22), С. 9884 - 9889

Опубликована: Апрель 27, 2020

Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of liquid, unbiased dibromoarenes under mechanochemical conditions selectively afford the monoarylated products. The lower reactivity crystalline products relative to liquid starting materials should be attributed predominantly low diffusion efficiency former in reaction mixture, which results a selective monoarylation. present study sheds light on novel approach using situ phase transitions solids design organic transformations that are difficult achieve via conventional solution-based synthesis.

Язык: Английский

Mechanochemical Phosphorylation of Polymers and Synthesis of Flame-Retardant Cellulose Nanocrystals DOI
Blaine G. Fiss,

Lucius Hatherly,

Robin S. Stein

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2019, Номер 7(8), С. 7951 - 7959

Опубликована: Март 15, 2019

Phosphorylated polymers are versatile materials for a broad range of applications from flame-retardant coatings to bioactive scaffolds. Traditionally, they synthesized in solution using corrosive concentrated phosphoric acid and energy-intensive drying techniques. In the past decade, mechanochemistry has proven be valuable tool green chemists conduct new transformations, with minimal waste, often solvent-free. This work presents phosphorylation cellulose nanocrystals, poly(ethylene glycol), poly(vinyl alcohol), chloride), lignin through mechanochemical processes phosphorus pentoxide produce reproducible potential applications. Through 31P magic angle spinning (MAS) NMR, loadings up 3300 mmol/kg were determined far superior around 1600 mmol/kg, 4375 obtained synthetic such as alcohol).

Язык: Английский

Процитировано

139

Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry DOI Creative Commons

Tamae Seo,

Tatsuo Ishiyama,

Koji Kubota

и другие.

Chemical Science, Год журнала: 2019, Номер 10(35), С. 8202 - 8210

Опубликована: Янв. 1, 2019

The first general solid-state Suzuki–Miyaura cross-coupling reactions using mechanochemistry has been developed.

Язык: Английский

Процитировано

131

Ball-free mechanochemistry: in situ real-time monitoring of pharmaceutical co-crystal formation by resonant acoustic mixing DOI Creative Commons
Adam A. L. Michalchuk∞, Karl S. Hope, Stuart R. Kennedy

и другие.

Chemical Communications, Год журнала: 2018, Номер 54(32), С. 4033 - 4036

Опубликована: Янв. 1, 2018

Resonant acoustic mixing (RAM) is a new technology designed for intensive of powders that offers the capability to process with minimal damage particles. This feature particularly important impact-sensitive materials such as explosives and propellants. While RAM technique has been extensively employed viscous polymers, comparatively little known about its use mechanosynthesis. We present here first in situ study RAM-induced co-crystallisation monitored using synchrotron X-ray powder diffraction. The phase profile reaction between nicotinamide carbamazepine presence small amount water was at two different relative accelerations mixer. In marked contrast ball-milling techniques, lack milling bodies experiment does not hinder starting materials, which occurred readily independent frequency oscillation. could be optimised by enhancing number reactive contacts through comminution. These observations provide insight into role various experimental parameters conventional mechanochemistry liquid-assisted grinding techniques.

Язык: Английский

Процитировано

105

Switching Chemoselectivity: Using Mechanochemistry to Alter Reaction Kinetics DOI Creative Commons

Joseph L. Howard,

Michael C. Brand, Duncan L. Browne

и другие.

Angewandte Chemie International Edition, Год журнала: 2018, Номер 57(49), С. 16104 - 16108

Опубликована: Окт. 18, 2018

Abstract A reaction manifold has been discovered in which the chemoselectivity can be altered by switching between neat milling and liquid assisted grinding (LAG) with polar additives. After investigation of mechanism, it established that this pathway is due to mechanochemical conditions exhibiting different kinetics for a key step transformation. This proof concept study demonstrates mechanochemistry used trap kinetic product reaction. It envisaged that, if successfully applied other transformations, novel synthetic processes could known pathways perturbed or diverted.

Язык: Английский

Процитировано

103

Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by in Situ Crystallization DOI

Tamae Seo,

Koji Kubota, Hajime Ito

и другие.

Journal of the American Chemical Society, Год журнала: 2020, Номер 142(22), С. 9884 - 9889

Опубликована: Апрель 27, 2020

Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of liquid, unbiased dibromoarenes under mechanochemical conditions selectively afford the monoarylated products. The lower reactivity crystalline products relative to liquid starting materials should be attributed predominantly low diffusion efficiency former in reaction mixture, which results a selective monoarylation. present study sheds light on novel approach using situ phase transitions solids design organic transformations that are difficult achieve via conventional solution-based synthesis.

Язык: Английский

Процитировано

99