(1-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Woerly, Eric M.; Miller, Jonathan E.; Burke, Martin D.

doi:10.1016/j.tet.2013.05.050

Cited by 35 publications

(23 citation statements)

References 55 publications

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“…Encouragingly,h undreds of MIDA-boronates are already commercially available and widely utilized. [102][103][104][105][106] Moreover,r ecent reports from many different research groups demonstrate that awide range of otherwise challenging-to-access MIDA-boronate building blocks can be prepared from MIDA-boronate starting materials. [91,93,96,[99][100][101][102][103][104][105][106][107] Leveraging the advances described below,there is also ample opportunity to automate the process of building-block synthesis,w hich has the potential to substantially increase the efficiency with which new building blocks can be sustainably accessed on demand.…”

Section: Angewandte Chemiementioning

confidence: 99%

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

2018

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The eighteenth and nineteenth centuries marked a sweeping transition from manual to automated manufacturing on the macroscopic scale. This enabled an unmatched period of human innovation that helped drive the Industrial Revolution. The impact on society was transformative, ultimately yielding substantial improvements in living conditions and lifespan in many parts of the world. During the same time period, the first manual syntheses of organic molecules was achieved. Now, two centuries later, we are poised for an analogous transition from highly customized crafting of specific molecular targets by hand to the increasingly general and automated assembly of many different types of molecules with the push of a button. Automation of customized small molecule synthesis pathways is already enabling safer, more reproducible, and readily scalable production of specific targets, and general machines now exist for the synthesis of a wide range of different peptides, oligonucleotides, and oligosaccharides. Creating general machines that are similarly capable of making many different types of small molecules on-demand, akin to that which has been achieved on the macroscopic scale with 3D printers, has proven to be substantially more challenging. Yet important progress is being made toward this potentially transformative objective with two complementary approaches: (1) automation of customized synthesis routes to different targets via machines that enable use of many different reactions and starting materials, and (2) automation of generalized platforms that make many different targets using common coupling chemistry and building blocks. Continued progress in these exciting directions has the potential to shift the bottleneck in molecular innovation from synthesis to imagination, and thereby help drive a new industrial revolution on the molecular scale.

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Section: Angewandte Chemiementioning

confidence: 99%

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

2018

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“…[98][99][100][101] Fürd en Erfolg dieses modularen Ansatzes ist ein einfacher Zugang zu den entsprechenden MIDA-Boronat-Bausteinen nçtig.Zurzeit sind bereits hunderte MIDA-Boronate kommerziell erhältlich und finden auch weit verbreitet Einsatz. [102][103][104][105][106] Zusätzlich zeigen neueste Entwicklungen von vielen verschiedenen Gruppen, dass eine große Bandbreite an schwer zugänglichen MIDA-Boronat-Bausteinen aus einfacheren MIDA-Boronat-Ausgangsmaterialien synthetisiert werden kann. [91,93,96,[99][100][101][102][103][104][105][106]107] Nutzt man alle zuvor beschrie-benen Methoden, finden sich genügend Mçglichkeiten, um die Synthese von Bausteinen zu automatisieren, wodurch der Zugang zu neuen Bausteinen substanziell beschleunigt werden kçnnte.…”

Section: Angewandte Chemieunclassified

Die molekulare industrielle Revolution: zur automatisierten Synthese organischer Verbindungen

Trobe

Burke

2018

Angewandte Chemie

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Derzeitkündigt sichein Wandel von der manuellen Synthese spezifischer Moleküle,die über individuell angepasste Routen verläuft, hin zu automatisch zusammenfügten Verbindungen unterschiedlichster Klassen mit nur einem Knopfdruckan. Die Entwicklung einer Maschine fürdie Herstellung unterschiedlichsterorganischer Moleküle je nachBedarf ist eine komplexe Aufgabe,e ss ind aber bereits bedeutende Fortschritte auf Basis von zwei komplementären Ansätzen zu verzeichnen:1 )Automatisierung individueller Routen fürdie Synthese diverser Verbindungen, wobei viele unterschiedliche Reaktionstypen und spezifische Reagentien genutzt werden kçnnen, und 2) Automatisierung einer generellen Plattform, die die Herstellung unterschiedlicher Verbindungen ausgehend von diversen Bausteinen, die mit derselben Kupplungsreaktion verknüpft werden, ermçglicht. Fortschritte in diesen Bereichen bieten die Mçglichkeit, Synthese-Engpässe zu vermeiden und den Fokus molekularer Innovation auf die Entwicklung neuer Methoden zu lenken und so eine "molekulare industrielle Revolution" zu beschleunigen.

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“…(2)] and this process is limited to C(sp 2 )b oronic acids as starting materials. [14] Recently,w ed eveloped Pd-catalyzed conjunctive crosscoupling reactions between an organoboronic ester,avinyllithium reagent, and aC (sp 2 )t riflate to give chiral organoboronic esters with high levels of enantiopurity. [15] This reaction has been expanded to include the use of Grignard reagents and C(sp 2 )halide electrophiles, [16] alkenyl migrating groups, [17] and has extended to nickel catalysts with both aryl [18] and alkyl electrophiles.…”

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confidence: 99%

“…With these modifications,3 -phenylpropyl (10)a nd n-octyl (11)m igrating groups were tolerated, as was asilyl ether (12). Ther eaction was also effective with cyclic substrates,including cyclopentyl (13), cyclohexyl (14), and N-Boc-protected piperidine (15) migrating groups.Migrating groups bearing potentially sensitive functional groups such as am onosubstituted olefin (16), amide (17), ester (18), or acetal (19)were also well-tolerated in this reaction. While examples in Table 2s uggest that the reaction is effective with Grignard-derived "ate" complexes, it should be noted that alkyllithium derived "ate" complexes often offer superior reactivity such that catalyst loading can be reduced to 1mol %Pd, with many substrates still achieving complete conversion in one hour (10)(11)(12).…”

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confidence: 99%