Continuous Flow Decarboxylative Monofluoroalkylation Enabled by Photoredox Catalysis

JACS Au, Год журнала: 2025, Номер 5(2), С. 684 - 692

Опубликована: Фев. 2, 2025

Herein, we report a scalable and mild strategy for the monofluoroalkylation of wide array Giese acceptors via visible-light-mediated photoredox catalysis in continuous flow. The use flow technology significantly enhances productivity scalability, whereas mildness conditions functional group tolerance are ensured by leveraging 4CzIPN, transition-metal-free organic photocatalyst. Structurally diverse secondary tertiary monofluoroalkyl radicals can thus be accessed from readily available α-monofluorocarboxylic acids. Given reaction conditions, this protocol is also amenable to late-stage functionalization biologically relevant molecules such as menthol, amantadine, bepotastine, estrone derivatives, rendering it suitable application drug discovery programs, which introduction fluorinated fragments highly sought after. This method was extended enable reductive multicomponent radical-polar crossover transformation rapidly increase complexity assembled architectures single synthetic operation.

Язык: Английский

---

Generation and Use of Bicyclo[1.1.0]butyllithium under Continuous Flow Conditions

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

The bicyclo[1.1.0]butyl scaffold has emerged as a valuable bioisostere in drug discovery programs. Here, we present streamlined approach for the generation of bicyclo[1.1.0]butyllithium and its functionalization with various classes electrophiles one-flow process, eliminating need intermediate isolation. In comparison to traditional batch processes, flow method allows use single organolithium reagent instead two operates at significantly higher temperatures (0 °C versus −78 °C), enhancing both practicality scalability.

Язык: Английский

---

Strained spiro heterocycles as potential bioisosteres: an update on the synthesis of heteroatom-containing spiro[2.3]hexanes and spiro[3.3]heptanes

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Developments in the synthesis and application of strained spiro heterocycles are discussed, given their potential as non-classical rigid three-dimensional bioisosteres drug development.

Язык: Английский

---

Generation and Use of Cyclopropenyllithium under Continuous Flow Conditions

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

The cyclopropene scaffold has emerged as a valuable platform in modern synthesis. Here, we present streamlined flow-based approach for the generation of cyclopropenyllithium and its functionalization with various electrophiles single, continuous flow process. This method eliminates need laborious temperature changes cryogenic conditions, significantly reduces process time from starting material to products. Compared traditional batch processes, our enables use single organolithium reagent operates efficiently at 0 °C, avoiding cool-warm-cool cycles typical methods. not only simplifies workflow but also enhances practicality, scalability, extends accessible chemical space.

Язык: Английский

---

Efficient synthesis of m-terphenyl compounds in continuous flow utilizing organomagnesium

Journal of Flow Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 26, 2025

Язык: Английский

---

Phosphine Catalyzed Enationselective and Diastereodivergent [3+2] Cyclization for Construction of Oxetane Dispirooxindole Skeletons

Chemical Communications, Год журнала: 2024, Номер 60(77), С. 10736 - 10739

Опубликована: Янв. 1, 2024

We have developed a phosphine catalyzed asymmetric [3+2] cyclization of 3-oxetanone derived MBH carbonates with activated methyleneoxindole, to construct oxetane dispirooxindole skeletons. Diastereodivergent synthesis was realized

Язык: Английский

---

‘Flash-Flow’ Generation and Exploitation of 3-Oxetanyllithium as a Reactive Nucleophile

Synfacts, Год журнала: 2024, Номер 20(07), С. 0683 - 0683

Опубликована: Июнь 14, 2024

Key words oxetanes - bioisosteres flash-flow spirocycles late-stage functionalization

Язык: Английский

---

Rapid and practical synthesis of N-protected amino ketones in continuous flow via pre-deprotonation protocol

Journal of Flow Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 18, 2024

Язык: Английский

---

Towards an approach to small-scale aryllithium flash flow chemistry using low-cost, low volume reactors

Journal of Flow Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 7, 2024

Язык: Английский

---