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

James A. K. Cochrane,

Aaron Rigby,

Raminder S. Mulla

et al.

Journal of Flow Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Language: Английский

Continuous Flow Decarboxylative Monofluoroalkylation Enabled by Photoredox Catalysis DOI Creative Commons

F Pasca,

Yuri Gelato,

Michael Andresini

et al.

JACS Au, Journal Year: 2025, Volume and Issue: 5(2), P. 684 - 692

Published: Feb. 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.

Language: Английский

Citations

3
Generation and Use of Bicyclo[1.1.0]butyllithium under Continuous Flow Conditions DOI Creative Commons
Elena Graziano, Marco Colella, Marcus Baumann

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

Citations

0
Strained spiro heterocycles as potential bioisosteres: an update on the synthesis of heteroatom-containing spiro[2.3]hexanes and spiro[3.3]heptanes DOI Creative Commons
Philipp Natho, Marco Colella, Renzo Luisi

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 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.

Language: Английский

Citations

0
Generation and Use of Cyclopropenyllithium under Continuous Flow Conditions DOI Creative Commons
Francesco Soddu,

Iktedar Mahdi,

Maria Chiara Cabua

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 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.

Language: Английский

Citations

0
Efficient synthesis of m-terphenyl compounds in continuous flow utilizing organomagnesium DOI
Chaoming Liang,

Weixia Lin,

Runxiang Yu

et al.

Journal of Flow Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 26, 2025

Language: Английский

Citations

0
Phosphine Catalyzed Enationselective and Diastereodivergent [3+2] Cyclization for Construction of Oxetane Dispirooxindole Skeletons DOI
Xiao Han, Jie Hou, Haiyan Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(77), P. 10736 - 10739

Published: Jan. 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

Language: Английский

Citations

2
‘Flash-Flow’ Generation and Exploitation of 3-Oxetanyllithium as a Reactive Nucleophile DOI
Paul Richardson

Synfacts, Journal Year: 2024, Volume and Issue: 20(07), P. 0683 - 0683

Published: June 14, 2024

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

Language: Английский

Citations

0
Rapid and practical synthesis of N-protected amino ketones in continuous flow via pre-deprotonation protocol DOI

Weixia Lin,

Zilong Lin,

Chaoming Liang

et al.

Journal of Flow Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

Language: Английский

Citations

0
Towards an approach to small-scale aryllithium flash flow chemistry using low-cost, low volume reactors DOI

James A. K. Cochrane,

Aaron Rigby,

Raminder S. Mulla

et al.

Journal of Flow Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Language: Английский

Citations

0