Fluoroalkynylations of Aryl Halides under Continuous-Flow Homogeneous Catalysis

Michael S. Placzek; Jessica M. Chmielecki; Connor Houghton; Alyssa Calder; Charlotte Wiles; Graham B. Jones

doi:10.1556/jfc-d-13-00004

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Journal of Flow Chemistry

Volume/Issue:: Volume 3: Issue 2

Fluoroalkynylations of Aryl Halides under Continuous-Flow Homogeneous Catalysis

Authors:

Michael S. Placzek

Michael S. Placzek Biorganic and Medicinal Chemistry Laboratories, Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA, 02115, USA

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Jessica M. Chmielecki

Jessica M. Chmielecki Biorganic and Medicinal Chemistry Laboratories, Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA, 02115, USA

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Connor Houghton

Connor Houghton Biorganic and Medicinal Chemistry Laboratories, Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA, 02115, USA

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Alyssa Calder

Alyssa Calder Biorganic and Medicinal Chemistry Laboratories, Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA, 02115, USA

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Charlotte Wiles

Charlotte Wiles Chemtrix BV, Burgemeester Lemmenstraat 358, 6163 JT, Geleen, The Netherlands

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Graham B. Jones

Graham B. Jones Biorganic and Medicinal Chemistry Laboratories, Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA, 02115, USA

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Pages:: 46–50

Online Publication Date:: 19 Jun 2013

Publication Date:: 19 Jun 2013

Article Category:: Research Article

DOI:: https://doi.org/10.1556/jfc-d-13-00004

Keywords:: flow chemistry; microfluidics; fluorine; positron emission tomography; Sonogashira coupling

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Abstract

Continuous-flow methodologies have been applied to the synthesis of a number of fluorinated alkynyl arenes and heteroarenes. Through a series of optimizations reagent stoichiometry and reaction time were improved and substrate specificity was interrogated. Using optimized conditions under copper-free Sonogashira type couplings readily available arene building blocks were derivatized with fluoroalkynyl side chains in <10 min. Given the rapidity of the process and the enhanced purity profile of the products an immediate application of the work is in the development of ¹⁸F labeled versions of the agents for subsequent use in positron emission tomography (PET) imaging. A homolog of the Alzheimer's disease imaging agent Fallypride^® was prepared using the methodology and additional analogs was identified.

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)