Manufacturing Process Development for Belzutifan, Part 2: A Continuous Flow Visible-Light-Induced Benzylic Bromination

Bottecchia, Cecilia; Lévesque, François; McMullen, Jonathan P.; Ji, Yining; Reibarkh, Mikhail; Peng, Feng; Tan, Lushi; Spencer, Glenn; Nappi, Jarod; Lehnherr, Dan; Narsimhan, Karthik; Wismer, Michael K.; Chen, Like; Lin, Yipeng; Dalby, Stephen M.

doi:10.1021/acs.oprd.1c00240

Cited by 61 publications

(54 citation statements)

References 29 publications

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“…[110] In addition, these systems are ideal models for standardized operation, and they facilitate transfer of light-driven processes to a technical scale. [97,[111][112][113]…”

Section: Scientific Perspectivementioning

confidence: 99%

Comparative Evaluation of Light‐Driven Catalysis: A Framework for Standardized Reporting of Data**

et al. 2022

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Light-driven homogeneous and heterogeneous catalysis require a complex interplay between light absorption, charge separation, charge transfer, and catalytic turnover. Optical and irradiation parameters as well as reaction engineering aspects play major roles in controlling catalytic performance. This multitude of factors makes it difficult to objectively compare light-driven catalysts and provide an unbiased performance assessment. This Scientific Perspective highlights the importance of collecting and reporting experimental data in homogeneous and heterogeneous light-driven catalysis. A critical analysis of the benefits and limitations of the commonly used experimental indicators is provided. Data collection and reporting according to FAIR principles is discussed in the context of future automated data analysis. The authors propose a minimum dataset as a basis for unified collecting and reporting of experimental data in homogeneous and heterogeneous light-driven catalysis. The community is encouraged to support the future development of this parameter list through an open online repository.

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“…[110] In addition, these systems are ideal models for standardized operation, and they facilitate transfer of light-driven processes to a technical scale. [97,[111][112][113]…”

Section: Scientific Perspectivementioning

confidence: 99%

Comparative Evaluation of Light‐Driven Catalysis: A Framework for Standardized Reporting of Data**

et al. 2022

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“…The protection of ketone via ketalization and the selective bromination by (1,3-Dibromo-5,5-Dimethylhydantoin, DBDMH) via a photochemical process at room temperature afforded 88 [ 54 ]. The subsequent oxidation was carried out via using 2-picoline N -oxide as the oxidizing agent in Kornblum-type oxidation to give the ketone 89 .…”

Section: New Halogen-containing Drugsmentioning

confidence: 99%

New Halogen-Containing Drugs Approved by FDA in 2021: An Overview on Their Syntheses and Pharmaceutical Use

et al. 2022

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This review describes the recent Food and Drug Administration (FDA)-approved drugs (in the year 2021) containing at least one halogen atom (covalently bound). The structures proposed throughout this work are grouped according to their therapeutical use. Their synthesis is presented as well. The number of halogenated molecules that are reaching the market is regularly preserved, and 14 of the 50 molecules approved by the FDA in the last year contain halogens. This underlines the emergent role of halogens and, in particular, of fluorine and chlorine in the preparation of drugs for the treatment of several diseases such as viral infections, several types of cancer, cardiovascular disease, multiple sclerosis, migraine and inflammatory diseases such as vasculitis.

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“…Similarly, we excluded those reports where the formation of the halogen atom does not depend on a photocatalyst, but is a consequence of photoinitiated and photochemical events. [37][38][39][40][41] Finally, we did not consider those cases where one of the substrates also works as the photocatalyst, [42] as these should be more properly referred to as photochemical approaches. It is worth mentioning that halogen radical-mediated HAT has been…”

Section: Introductionmentioning

confidence: 99%

Synthetic Applications of Photocatalyzed Halogen‐Radical Mediated Hydrogen Atom Transfer for C−H Bond Functionalization

2022

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The opportunity to activate C(sp3)−H bonds via homolytic cleavage by means of halogen radicals has long been disregarded in synthetic endeavors due to the unpredictable selectivity. Nowadays, photocatalysis has established itself as a method of choice for the generation of such reactive intermediates under mild conditions. This Minireview collects recent examples showcasing how photocatalytic manifolds have been used to tame aggressive halogen radicals to activate C(sp3)−H bonds via Hydrogen Atom Transfer (HAT) for synthetic purposes. In the last section of this work, we address site‐selectivity issues posed by this methodology and show how it can be guided through the judicious choice of reaction conditions.

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Manufacturing Process Development for Belzutifan, Part 2: A Continuous Flow Visible-Light-Induced Benzylic Bromination

Cited by 61 publications

References 29 publications

Comparative Evaluation of Light‐Driven Catalysis: A Framework for Standardized Reporting of Data**

Comparative Evaluation of Light‐Driven Catalysis: A Framework for Standardized Reporting of Data**

New Halogen-Containing Drugs Approved by FDA in 2021: An Overview on Their Syntheses and Pharmaceutical Use

Synthetic Applications of Photocatalyzed Halogen‐Radical Mediated Hydrogen Atom Transfer for C−H Bond Functionalization

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