Juan A. Rincón

The History of Flow Chemistry at Eli Lilly and Company

Martin D. Johnson, Timothy M. Braden, Joel R. Calvin, Alison Campbell Brewer et autres

Flow chemistry was initially used for speed to early phase material delivery in the development laboratories, scaling up chemical transformations that we would not or could not scale up batch for safety reasons. Some early examples included a Newman Kwart Rearrangement, Claisen …

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Continuous-Flow Supercritical CO 2 Platform for In-Situ Synthesis and Purification of Small Molecules for Drug Discovery

Sergio Alcalde, Raúl Porcar, Marı́a Luz de la Puente, Graham R. Cumming et autres

The use of supercritical CO 2 (scCO 2 ) as an enabling technology paves the way for an efficient in-line integration of the synthesis and purification of organic molecules. The scCO 2 platform presented here provides a streamlined process to produce a …

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Flow photochemical Giese reaction via silane-mediated activation of alkyl bromides

Fabiola Fanini, Alberto Luridiana, Daniele Mazzarella, Antonella Ilenia Alfano et autres

Organic halides play a key role as building blocks in synthesis because of their low cost and wide availability. In recent years, halogen-atom transfer (XAT) has emerged as a reliable approach to exploit these substrates in radical processes. Herein, we report a …

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The Merger of Benzophenone HAT Photocatalysis and Silyl Radical-Induced XAT Enables Both Nickel-Catalyzed Cross-Electrophile Coupling and 1,2-Dicarbofunctionalization of Olefins

Alberto Luridiana, Daniele Mazzarella, Luca Capaldo, Juan A. Rincón et autres

) bonds. The mild protocol is fast and scalable using flow technology, displays broad functional group tolerance, and is amenable to a wide variety of medicinally relevant moieties. Mechanistic investigations reveal that the ketone catalyst, upon photoexcitation, is responsible for the direct …

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Automated Flow Chemistry Platforms

Juan A. Rincón, María José Nieves‐Remacha, Carlos Mateos

In this chapter, the authors want to highlight the recent progress in automated flow chemistry platforms with direct application to Medicinal Chemistry. The utility of monitoring techniques and intelligent algorithms to build autonomous platforms enabling self-optimized processes is also discussed.

Continuous stirred-tank reactor cascade platform for self-optimization of reactions involving solids

Kakasaheb Y. Nandiwale, Travis Hart, Andrew F. Zahrt, Anirudh M. K. Nambiar et autres

Research-scale fully automated flow platform for reaction self-optimization with solids handling facilitates identification of optimal conditions for continuous manufacturing of pharmaceuticals while reducing amounts of raw materials consumed.

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Accelerated and Scalable C(sp 3 )–H Amination via Decatungstate Photocatalysis Using a Flow Photoreactor Equipped with High-Intensity LEDs

Ting Wan, Zhenghui Wen, Gabriele Laudadio, Luca Capaldo et autres

High Resolution Image Download MS PowerPoint Slide Carbon–nitrogen bonds are ubiquitous in biologically active compounds, prompting synthetic chemists to design various methodologies for their preparation. Arguably, the ideal synthetic approach is to be able to directly convert omnipresent C–H bonds in organic …

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Self-Optimization of Continuous Flow Electrochemical Synthesis Using Fourier Transform Infrared Spectroscopy and Gas Chromatography

Jie Ke, Chuang Gao, Ana A. Folgueiras‐Amador, Katherine E. Jolley et autres

A continuous-flow electrochemical synthesis platform has been developed to enable self-optimization of reaction conditions of organic electrochemical reactions using attenuated total reflection Fourier transform infrared spectroscopy (ATR FT-IR) and gas chromatography (GC) as online real-time monitoring techniques. We have overcome the challenges …

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Hybrid Flow-Batch Model for the Efficient Synthesis of 2-(Dimethylamino)-6-methylpyridin-4-ol

Juan A. Rincón, Antonio Navarro, María José Nieves‐Remacha, José Eugenio de Diego et autres

A practical and scalable method for the synthesis of 2-(dimethylamino)-6-methylpyridin-4-ol is described. Despite its structural simplicity, the synthesis and isolation of this molecule in useful yields has proven to be challenging. A hybrid-flow (flow–batch–flow) mode approach was designed to circumvent issues associated …

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Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

Tomer M. Faraggi, Caroline Rouget-Virbel, Juan A. Rincón, Mario Barberis et autres

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial …

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Rapid Optimization of Photoredox Reactions for Continuous-Flow Systems Using Microscale Batch Technology

María González‐Esguevillas, David F. Fernández, Juan A. Rincón, Mario Barberis et autres

Photoredox catalysis has emerged as a powerful and versatile platform for the synthesis of complex molecules. While photocatalysis is already broadly used in small-scale batch chemistry across the pharmaceutical sector, recent efforts have focused on performing these transformations in process chemistry due …

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Decatungstate‐Mediated C(sp3)–H Heteroarylation via Radical‐Polar Crossover in Batch and Flow

Ting Wan, Luca Capaldo, Gabriele Laudadio, Alexander V. Nyuchev et autres

Abstract Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)–H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical–polar crossover concept to access the direct net‐oxidative …

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