Literature DB >> 15926844

A microreactor for microwave-assisted capillary (continuous flow) organic synthesis.

Eamon Comer1, Michael G Organ.   

Abstract

A capillary-based flow system has been developed for conducting microscale organic synthesis with the aid of microwave irradiation. The capillary internal diameter investigated ranged from 200 to 1200 mum, while the flow rate was varied between 2 and 40 muL/min, which corresponds to the sample being irradiated approximately 4 min. Other parameters investigated include reaction concentration and power setting of the microwave. Excellent conversion was observed in a variety of cross coupling and ring-closing metathesis (RCM) reactions employing metal catalysts and in nucleophilic aromatic substitution and Wittig reactions that do not employ metals. Reactions that have solids in them do not seem to pose a significant concern for the method, such as blocked channels. It was shown that capillaries coated internally with thin films of Pd metal show tremendous rate accelerations and that the thin films themselves are capable of catalyzing Suzuki-Miyaura reactions with no exogenous catalyst added. Importantly, it has been demonstrated that reagents in separate syringes can be coinjected into the capillary, mix, and react with none of the laminar flow problems that plague microreactor (lab on a chip) technology. This paves the way to use microwave-assisted, flow capillary synthesis as a powerful and efficient means to replace "one-at-a-time" microwave synthesis to provide libraries of compounds in a scale suitable for biological screening purposes.

Entities:  

Year:  2005        PMID: 15926844     DOI: 10.1021/ja0512069

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

1.  High-load, hybrid Si-ROMP reagents.

Authors:  Alan Rolfe; Joanna K Loh; Pradip K Maity; Paul R Hanson
Journal:  Org Lett       Date:  2010-12-01       Impact factor: 6.005

2.  Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

Authors:  Qin Zang; Salim Javed; Farman Ullah; Aihua Zhou; Christopher A Knudtson; Danse Bi; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  Synthesis (Stuttg)       Date:  2011-09-01       Impact factor: 3.157

3.  In situ generation and intramolecular Schmidt reaction of keto azides in a microwave-assisted flow format.

Authors:  Thomas O Painter; Paul D Thornton; Mario Orestano; Conrad Santini; Michael G Organ; Jeffrey Aubé
Journal:  Chemistry       Date:  2011-07-27       Impact factor: 5.236

4.  Synthesis of amino-benzothiaoxazepine-1,1-dioxides utilizing a microwave-assisted, S(N)Ar protocol.

Authors:  Alan Rolfe; Farman Ullah; Thiwanka B Samarakoon; Ryan D Kurtz; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-09-08       Impact factor: 3.784

5.  The development of a general strategy for the synthesis of tyramine-based natural products by using continuous flow techniques.

Authors:  Srinivas Achanta; Virginie Liautard; Robert Paugh; Michael G Organ
Journal:  Chemistry       Date:  2010-11-15       Impact factor: 5.236

6.  Scaling out by microwave-assisted, continuous flow organic synthesis (MACOS): multi-gram synthesis of bromo- and fluoro-benzofused sultams benzthiaoxazepine-1,1-dioxides.

Authors:  Farman Ullah; Thiwanka Samarakoon; Alan Rolfe; Ryan D Kurtz; Paul R Hanson; Michael G Organ
Journal:  Chemistry       Date:  2010-09-24       Impact factor: 5.236

7.  Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS).

Authors:  Farman Ullah; Qin Zang; Salim Javed; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson; Michael G Organ
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

8.  Scaling up of continuous-flow, microwave-assisted, organic reactions by varying the size of Pd-functionalized catalytic monoliths.

Authors:  Ping He; Stephen J Haswell; Paul D I Fletcher; Stephen M Kelly; Andrew Mansfield
Journal:  Beilstein J Org Chem       Date:  2011-08-23       Impact factor: 2.883

9.  Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl(3) promoted homocoupling.

Authors:  Aiichiro Nagaki; Yuki Uesugi; Yutaka Tomida; Jun-Ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2011-08-02       Impact factor: 2.883

10.  Gold film-catalysed benzannulation by microwave-assisted, continuous flow organic synthesis (MACOS).

Authors:  Gjergji Shore; Michael Tsimerman; Michael G Organ
Journal:  Beilstein J Org Chem       Date:  2009-07-21       Impact factor: 2.883

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