Polymer‐Supported Organosuperbases

Kotsuki, Hiyoshizo

doi:10.1002/9780470740859.ch6

Cited by 5 publications

(1 citation statement)

References 80 publications

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“…The chemistry of supported polymers and reagents has been developed significantly in recent years, and this has provided excellent solutions. One example is the development of supported superbases on polymeric supports, many of which are commercially available . Therefore, from a practical point of view, it is also interesting to develop one-pot procedures that combine the use of monoliths, magnetic nanoparticles, and supported reagents, thus enabling immobilization, control of catalyst oxidation states, compartmentation, and individual recovery of the precious catalysts.…”

Section: Introductionmentioning

confidence: 99%

Multicatalysis Combining 3D-Printed Devices and Magnetic Nanoparticles in One-Pot Reactions: Steps Forward in Compartmentation and Recyclability of Catalysts

Díaz-Marta

Yáñez

Tubío

et al. 2019

ACS Appl. Mater. Interfaces

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A tricatalytic compartmentalized system that immobilizes metallic species to perform one-pot sequential functionalization is described: a three-dimensional (3D)-printed palladium monolith, ferritic copper(I) magnetic nanoparticles, and a 3D-printed polypropylene capsule-containing copper(II) loaded onto polystyrene-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PS-TBD) allowed the rapid synthesis of diverse substituted 1-([1,1′-biphenyl]-4-yl)-1H-1,2,3-triazoles. The procedure is based on the Chan−Lam azidation/copper alkyne−azide cycloaddition/Suzuki reaction strategy in the solution phase. This catalytic system enabled the efficient assembly of the final compounds in high yields without the need for special additives or intermediate isolation. The monolithic catalyst-containing immobilized palladium species was synthesized by surface chemical modification of a 3D-printed silica monolith using a soluble polyimide resin as a key reagent, thus creating an extremely robust composite. All three immobilized catalysts described here were easily recovered and reused in numerous cycles. This work exemplifies the role of 3D printing in the design and manufacture of devices for compartmented multicatalytic systems to carry out complex one-pot transformations.

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Section: Introductionmentioning

confidence: 99%

Multicatalysis Combining 3D-Printed Devices and Magnetic Nanoparticles in One-Pot Reactions: Steps Forward in Compartmentation and Recyclability of Catalysts

Díaz-Marta

Yáñez

Tubío

et al. 2019

ACS Appl. Mater. Interfaces

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Accelerated SuFEx Click Chemistry For Modular Synthesis**

et al. 2021

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SuFEx click chemistry is ap owerful method designed for the selective,r apid, and modular synthesis of functional molecules.Classical SuFEx reactions form stable SÀ Ol inkages upon exchange of SÀFb onds with aryl silyl-ether substrates,a nd while near-perfect in their outcome,a re sometimes disadvantaged by relatively high catalyst loadings and prolonged reaction times.W eherein report the development of accelerated SuFEx clickc hemistry (ASCC), an improved SuFEx method for the efficient and catalytic coupling of aryl and alkyla lcohols with ar ange of SuFExable hubs.W e demonstrate Bartonsh indered guanidine base (2-tert-butyl-1,1,3,3-tetramethylguanidine;B TMG) as as uperb SuFEx catalyst that, when used in synergy with silicon additive hexamethyldisilazane (HMDS), yields stable S À Ob ond linkages in as ingle step;o ften within minutes.T he powerful combination of BTMG and HMDS reagents allows for catalyst loadings as lowa s1 .0 mol %a nd, in congruence with clickprinciples,provides ascalable method that is safe,efficient, and practical for modular synthesis.ASSC expands the number of accessible SuFEx products and will find significant application in organic synthesis,m edicinal chemistry,c hemical biology, and materials science.

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Accelerated SuFEx Click Chemistry For Modular Synthesis**

et al. 2021

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SuFEx click chemistry is a powerful method designed for the selective, rapid, and modular synthesis of functional molecules. Classical SuFEx reactions form stable S−O linkages upon exchange of S−F bonds with aryl silyl‐ether substrates, and while near‐perfect in their outcome, are sometimes disadvantaged by relatively high catalyst loadings and prolonged reaction times. We herein report the development of accelerated SuFEx click chemistry (ASCC), an improved SuFEx method for the efficient and catalytic coupling of aryl and alkyl alcohols with a range of SuFExable hubs. We demonstrate Barton's hindered guanidine base (2‐tert‐butyl‐1,1,3,3‐tetramethylguanidine; BTMG) as a superb SuFEx catalyst that, when used in synergy with silicon additive hexamethyldisilazane (HMDS), yields stable S−O bond linkages in a single step; often within minutes. The powerful combination of BTMG and HMDS reagents allows for catalyst loadings as low as 1.0 mol % and, in congruence with click‐principles, provides a scalable method that is safe, efficient, and practical for modular synthesis. ASSC expands the number of accessible SuFEx products and will find significant application in organic synthesis, medicinal chemistry, chemical biology, and materials science.

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Polymer‐Supported Organosuperbases

Cited by 5 publications

References 80 publications

Multicatalysis Combining 3D-Printed Devices and Magnetic Nanoparticles in One-Pot Reactions: Steps Forward in Compartmentation and Recyclability of Catalysts

Multicatalysis Combining 3D-Printed Devices and Magnetic Nanoparticles in One-Pot Reactions: Steps Forward in Compartmentation and Recyclability of Catalysts

Accelerated SuFEx Click Chemistry For Modular Synthesis**

Accelerated SuFEx Click Chemistry For Modular Synthesis**

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