scholarly journals Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

2016 ◽  
Vol 7 (6) ◽  
pp. 3676-3680 ◽  
Author(s):  
Kai Chen ◽  
Shuai Zhang ◽  
Pei He ◽  
Pengfei Li
Keyword(s):  
Continuous Flow ◽  
Aryl Halides ◽  
Flow Conditions ◽  
Metal Free ◽  
Bond Forming

A metal-free C–B bond forming reaction of aryl halides under batch and continuous-flow conditions is described.

scholarly journals The Eschenmoser coupling reaction under continuous-flow conditions

2011 ◽  
Vol 7 ◽  
pp. 1164-1172 ◽  
Author(s):  
Sukhdeep Singh ◽  
J Michael Köhler ◽  
Andreas Schober ◽  
G Alexander Groß
Keyword(s):  
Continuous Flow ◽  
Elevated Temperatures ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Flow Chemistry ◽  
Flow Conditions ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

The Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Eschenmoser coupling needs prolonged reaction times and elevated temperatures to deliver valuable yields. We have used a flow chemistry system to promote the Eschenmoser coupling under enhanced reaction conditions in order to convert the demanding precursors such as S-alkylated secondary thioamides and thiolactames in an efficient way. Under pressurized reaction conditions at about 220 °C, the desired Eschenmoser coupling products were obtained within 70 s residence time. The reaction kinetics was investigated and 15 examples of different building block combinations are given.

Metal-free hydroxylation of tertiary ketones under intensified and scalable continuous flow conditions

2020 ◽  
Vol 10 (1) ◽  
pp. 167-179 ◽  
Author(s):  
Victor-Emmanuel H. Kassin ◽  
Thomas Toupy ◽  
Guillaume Petit ◽  
Pauline Bianchi ◽  
Elena Salvadeo ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Flow Conditions ◽  
Metal Free

A metal-free synthesis of 1,1-diphenylvinylsulfides with thiols via thioetherification under continuous-flow conditions

2020 ◽  
Vol 7 (12) ◽  
pp. 1490-1494 ◽  
Author(s):  
Jiawei Zhang ◽  
Erfei Wang ◽  
Yang Zhou ◽  
Lu Zhang ◽  
Mao Chen ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Flow Chemistry ◽  
Flow Conditions ◽  
Aggregation Induced Emission ◽  
Metal Free ◽  
Mild Conditions ◽  
Continuous Flow Chemistry ◽  
Efficient Access

A continuous-flow chemistry facilitated protocol that allows efficient access to a novel aggregation-induced emission (AIE) luminogen 1,1-diphenylvinylsulfides utilizing thiols under metal-free and mild conditions.

scholarly journals Development of an efficient and sustainable synthesis of 2-(3-methyl-1H-1,2,4-triazol-1-yl) acetic acid under continuous-flow conditions

2020 ◽  
Vol 22 (12) ◽  
pp. 3748-3758 ◽  
Author(s):  
Simone Tortoioli ◽  
Astrid Friedli ◽  
Alice Prud'homme ◽  
Sylvia Richard-Bildstein ◽  
Philipp Kohler ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Continuous Flow ◽  
Triazole Ring ◽  
Flow Conditions ◽  
Metal Free ◽  
Free Process ◽  
Efficient Construction

A novel, metal-free process for the challenging synthesis of 1,2,4-triazoles is reported, which features an efficient construction of the triazole ring under flow conditions.

scholarly journals Development of an Efficient and Sustainable Synthesis of 2-(3-Methyl-1H-1,2,4-Triazol-1-Yl) Acetic Acid Under Continuous-Flow Conditions

2020 ◽  
Author(s):  
Simone Tortoioli ◽  
Astrid Friedli ◽  
Alice Prud’homme ◽  
Sylvia Richard-Bildstein ◽  
Philipp Kohler ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Continuous Flow ◽  
Flow Reactor ◽  
Environmentally Benign ◽  
Sustainable Construction ◽  
Flow Conditions ◽  
Step Method ◽  
Metal Free ◽  
Free Process ◽  
Synthetic Routes

A novel, metal-free process for the challenging synthesis of 2-(3-methyl-1<i>H</i>-1,2,4-triazol-1-yl) acetic acid (<b>1</b>) is reported, which features an efficient condensation for the triazole build-up under flow conditions. This continuous, two-step method is atom economical, highly selective and environmentally benign, due to the avoidance of chromatography and isolation steps. Compared to the earlier batch synthetic routes, higher yields were achieved in a flow reactor. In addition, a highly energetic intermediate could be controlled and handled in a safe manner. To generalize the established route, several triazoles were finally prepared under the described conditions, confirming that the methodology could find useful applications for the rapid and sustainable construction of differentially functionalized 1,2,4-triazoles.

scholarly journals A Continuous-Flow, Two-Step, Metal-Free Process for the Synthesis of Differently Substituted Chiral 1,2-Diamino Derivatives

Synthesis ◽  
2018 ◽  
Vol 50 (07) ◽  
pp. 1430-1438
Author(s):  
Maurizio Benaglia ◽  
Margherita Pirola ◽  
Maria Compostella ◽  
Laura Raimondi ◽  
Alessandra Puglisi
Keyword(s):  
Continuous Flow ◽  
Catalytic Synthesis ◽  
Flow Conditions ◽  
Reaction Conditions ◽  
Flow Process ◽  
Preliminary Screening ◽  
Metal Free ◽  
Free Process ◽  
Continuous Flow Process ◽  
Nitro Reduction

The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-μL microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereo­selective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.

scholarly journals Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane

2016 ◽  
Vol 12 ◽  
pp. 2614-2619 ◽  
Author(s):  
Riccardo Porta ◽  
Alessandra Puglisi ◽  
Giacomo Colombo ◽  
Sergio Rossi ◽  
Maurizio Benaglia
Keyword(s):  
Continuous Flow ◽  
Reaction Times ◽  
Nitro Compounds ◽  
Primary Amines ◽  
Flow Conditions ◽  
Metal Free ◽  
Nitro Derivatives ◽  
Aromatic Nitro ◽  
High Yields ◽  
First Time

The metal-free reduction of nitro compounds to amines mediated by trichlorosilane was successfully performed for the first time under continuous-flow conditions. Aromatic as well as aliphatic nitro derivatives were converted to the corresponding primary amines in high yields and very short reaction times with no need for purification. The methodology was also extended to the synthesis of two synthetically relevant intermediates (precursors of baclofen and boscalid).

scholarly journals Development of an Efficient and Sustainable Synthesis of 2-(3-Methyl-1H-1,2,4-Triazol-1-Yl) Acetic Acid Under Continuous-Flow Conditions

2020 ◽  
Author(s):  
Simone Tortoioli ◽  
Astrid Friedli ◽  
Alice Prud’homme ◽  
Sylvia Richard-Bildstein ◽  
Philipp Kohler ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Continuous Flow ◽  
Flow Reactor ◽  
Environmentally Benign ◽  
Sustainable Construction ◽  
Flow Conditions ◽  
Step Method ◽  
Metal Free ◽  
Free Process ◽  
Synthetic Routes

A novel, metal-free process for the challenging synthesis of 2-(3-methyl-1<i>H</i>-1,2,4-triazol-1-yl) acetic acid (<b>1</b>) is reported, which features an efficient condensation for the triazole build-up under flow conditions. This continuous, two-step method is atom economical, highly selective and environmentally benign, due to the avoidance of chromatography and isolation steps. Compared to the earlier batch synthetic routes, higher yields were achieved in a flow reactor. In addition, a highly energetic intermediate could be controlled and handled in a safe manner. To generalize the established route, several triazoles were finally prepared under the described conditions, confirming that the methodology could find useful applications for the rapid and sustainable construction of differentially functionalized 1,2,4-triazoles.

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