ChemInform Abstract: Development of a Direct Photocatalytic C—H Fluorination for the Preparative Synthesis of Odanacatib.

Halperin, Shira D.; Kwon, Daniel; Holmes, Michael; Regalado, Erik L.; Campeau, Louis‐Charles; DiRocco, Daniel A.; Britton, Robert

doi:10.1002/chin.201613062

Cited by 2 publications

(2 citation statements)

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“…To achieve this selectivity, careful tuning of the steric and electric properties of the HAT photocatalyst and substrate has to take place. Among the limited selection of photocatalysts promoting HAT, arguably the most versatile HAT photocatalyst is the decatungstate anion, which found application in a wide range of transformations, including alkylation, [3][4][5][6][7][8] arylation, 9 acylation, 10 amination [11][12][13][14] , fluorination, [15][16][17] trifluoromethylation, 18 sulfinylation 19 and oxygenation (Scheme 1A). 20,21 Despite the potential of TBADT for synthetic applications, the adoption of photocatalytic HAT in industrial processes is still limited.…”

Section: Introductionmentioning

confidence: 99%

Membrane-based TBADT recovery: increasing the sustainability of continuous-flow photocatalytic HAT transformations

Wen

Pintossi

Nuño³

et al. 2022

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Photocatalytic hydrogen atom transfer (HAT) processes have been the object of numerous studies showcasing the potential of the homogeneous photocatalyst tetrabutylammonium decatungstate (TBADT) for the functionalization of C(sp3)–H bonds. However, to translate these studies into large-scale industrial processes, careful considerations of catalyst consumption, cost, and removal are required. This work presents organic solvent nanofiltration (OSN) as the answer to reduce TBADT consumption, to increase its turnover number and to lower its concentration in the product solution, thus enabling large-scale photocatalytic HAT-based transformations. The operating parameters for a suitable membrane for TBADT recovery in acetonitrile were optimized. Continuous photocatalytic C(sp3)-H alkylation reactions were carried out with in-line TBADT recovery via two OSN steps. Promisingly, the observed product yields for the reactions with in-line catalyst recycling are comparable to those of reactions performed with pristine TBADT, therefore highlighting that not only catalyst recovery (>99%, TON > 6500) is a possibility, but also that it does not happen at the expense of reaction performance.

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Section: Introductionmentioning

confidence: 99%

Membrane-based TBADT recovery: increasing the sustainability of continuous-flow photocatalytic HAT transformations

Wen

Pintossi

Nuño³

et al. 2022

Preprint

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“…-1H-benzo[d]imidazol-2-yl)pyridin-2yl)-3-azaspiro[5.5]undecan-9-yl)acetic Acid(35).Procedure D was used to obtain the product. [MH] + m/z 473; 1 H NMR (DMSO-d 6 , 600 MHz) δ 1.05 (m, 4H), 1.39 (m, 2H), 1.53 (m, 4H), 1.71 (m, 3), 2.14 (d, J = 6.6 Hz, 1H), 2.25 (d, J = 6.6 Hz, 1H), 3.68 (m, 4H), 7.13 (m, 1H), 7.64 (d, J = 8.2 Hz, 1H), 7.84 (d, J = 8.5 Hz, 1H), 7.99 (s, 1H), 8.26 (d, J = 8.6 Hz, 1H), 8.89 (s, 1H).…”

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confidence: 99%

Microscale High-Throughput Experimentation as an Enabling Technology in Drug Discovery: Application in the Discovery of (Piperidinyl)pyridinyl-1H-benzimidazole Diacylglycerol Acyltransferase 1 Inhibitors

et al. 2017

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Miniaturization and parallel processing play an important role in the evolution of many technologies. We demonstrate the application of miniaturized high-throughput experimentation methods to resolve synthetic chemistry challenges on the frontlines of a lead optimization effort to develop diacylglycerol acyltransferase (DGAT1) inhibitors. Reactions were performed on ∼1 mg scale using glass microvials providing a miniaturized high-throughput experimentation capability that was used to study a challenging SAr reaction. The availability of robust synthetic chemistry conditions discovered in these miniaturized investigations enabled the development of structure-activity relationships that ultimately led to the discovery of soluble, selective, and potent inhibitors of DGAT1.

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ChemInform Abstract: Development of a Direct Photocatalytic C—H Fluorination for the Preparative Synthesis of Odanacatib.

Cited by 2 publications

References 1 publication

Membrane-based TBADT recovery: increasing the sustainability of continuous-flow photocatalytic HAT transformations

Membrane-based TBADT recovery: increasing the sustainability of continuous-flow photocatalytic HAT transformations

Microscale High-Throughput Experimentation as an Enabling Technology in Drug Discovery: Application in the Discovery of (Piperidinyl)pyridinyl-1H-benzimidazole Diacylglycerol Acyltransferase 1 Inhibitors

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