Examples of published literature for Coupling reactions

Visible‐Light‐Mediated Cross‐Couplings and C–H Activation via Dual Photoredox/Transition‐Metal Catalysis in Continuous‐Flow Processes

Soo Dong Kim, Jonghyun Lee, Nam-Jung Kim, Boyoung Park

  • Kyung Hee University, Department of Pharmacy, Kyungheedaero 26, 02447 Seoul, Republic of Korea
View abstract

A Photoredox Coupling Reaction of Benzylboronic Esters and Carbonyl Compounds in Batch and Flow

Yiding Chen, Oliver May, David C. Blakemore, and Steven V. Ley†*

  • Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
  • †‡ Medicine Design, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, United States
View abstract

Continuous preparation for rifampicin

Xin Li 1, Zhuang Liu 1, Zheng Fang 1, Hao Qi 1, Siyu Huang 1, Shanshan Miao 1, Kai Guo 1,2

  • 1 College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, China
  • 2 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing, China
View abstract

Photoinduced Palladium Negishi Cross-Coupling Through Visible Light Absorption of Palladium-Organozinc complexes

Irini Abdiaj a, Lena Huck a,b, José Miguel Mateo b, Antonio de la Hoz b, M. Victoria Gomez c, Angel Díaz-Ortiz b, Jesús Alcázar a

  • a Lead Discovery, Janssen Research and Development, Janssen-Cilag, S.A., Jarama 75A, 45007 Toledo, Spain
  • b Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La Mancha, Av. Camilo José Cela 10, 13071 Ciudad Real, Spain
  • c Instituto Regional de Investigación Científica Aplicada, Universidad de Castilla-La Mancha, Av. Camilo José Cela, sn, 13071 Ciudad Real, Spain
View abstract

Continuous flow synthesis of a carbon-based molecular cage macrocycle via a three-fold homocoupling reaction

Melanie Kitchinab, Kristina Konstasa, Christopher J. Sumbyb, Milena L. Czyza, Peter Valenteb, Matthew R. Hill*ab, Anastasios Polyzos*ac, Christian J. Doonan*ab

  • * Corresponding authors
  • a CSIRO Manufacturing Flagship, Bayview Avenue, Clayton, Australia
  • b Centre for Advanced Nanomaterials and the School of Physical Sciences, The University of Adelaide, Adelaide, Australia
View abstract

An efficient benzoxaborole one‐pot synthesis by SiliaCat DPP‐Pd heterogeneous catalysis using diboronic acid

Kana kunihiro1, Laurence Dumais2, Guillaume Lafitte2, Emeric Varvier2, Loïc Tomas2, Craig Harris2

  • 1 Ecole Nationale Supérieure des Ingenieurs en Arts Chimiques et Technologiques, France
  • 2 Nestlé Skin Health, Galderma R&D, France
View abstract

Functionalization of Heteroarenes Under Continuous Flow

Joachim Demaerel, Vidmantas Bieliũnas, Wim M. De Borggraeve

  • Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven, Belgium
View abstract

Photoredox Iridium–Nickel Dual-Catalyzed Decarboxylative Arylation Cross-Coupling: From Batch to Continuous Flow via Self-Optimizing Segmented Flow Reactor

Hsiao-Wu Hsieh, Connor W. Coley, Lorenz M. Baumgartner, Klavs F. Jensen*‡, Richard I. Robinson*†

  • Global Discovery Chemistry − Chemical Technology Group, Novartis Institutes for Biomedical Research, 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States
  • Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States
View abstract

Flow assisted synthesis: a key fragment of SR 142948A

Matthew Oliver Kitching, Olivia E Dixon, Marcus Baumann, Ian Richard Baxendale

  • University of Durham, Chemistry, Durham, UK
View abstract

Phase separation macrocyclization in a complex pharmaceutical setting: application toward the synthesis of vaniprevir

Eric Godin, Anne-Catherine Bédard, Michael Raymond, Shawn K. Collins*

  • Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec, H3C 3J7 Canada
View abstract

Improving the throughput of batch photochemical reactions using flow: Dual photoredox and nickel catalysis in flow for C(sp2) C(sp3) cross-coupling

Irini Abdiaj, Jesús Alcázar

  • Janssen Research and Development, Janssen-Cilag, S.A., C/Jarama 75, 45007 Toledo, Spain
View abstract

Synthesis of Cycloalkyl Substituted 7-Azaindoles via Photoredox Nickel Dual Catalytic Cross-Coupling in Batch and Continuous Flow

Natalie Palaychuk, Travis J. DeLano, Michael J. Boyd, Jeremy Green, and Upul K. Bandarage

  • Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States
View abstract

Application of the Photoredox Coupling of Trifluoroborates and Aryl Bromides to Analog Generation Using Continuous Flow

Travis J. DeLano, Upul K. Bandarage, Natalie Palaychuk, Jeremy Green, and Michael J. Boyd

  • Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States
View abstract

γ-Glutamyl-dipeptides: Easy tools to rapidly probe the stereoelectronic properties of the ionotropic glutamate receptor binding pocket

Lucia Tamborinia, Veronica Nicosiaa, Paola Contia, Federica Dall'Oglioa, Carlo De Michelia, Birgitte Nielsenb, Anders A. Jensenb, Darryl S. Pickeringb, Andrea Pintoa

  • a Department of Pharmaceutical Sciences (DISFARM), University of Milan, Via Mangiagalli 25, 20133 Milan, Italy
  • b Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen OE, Denmark
View abstract

Visible light activation of Boronic Esters enables efficient photoredox C(sp2)–C(sp3) cross-couplings in flow

Fabio Limaa, Dr. Mikhail A. Kabeshova, Dr. Duc N. Trana, Dr. Claudio Battilocchioa, Dr. Joerg Sedelmeierb, Dr. Gottfried Sedelmeierb, Dr. Berthold Schenkelb, S. V. Ley*a

  • * Corresponding author
  • a Department of Chemistry, University of Cambridge, Cambridge, UK
  • b Novartis Pharma AG, Basel, Switzerland
View abstract

Catalytic Chan–Lam coupling using a ‘tube-in-tube’ reactor to deliver molecular oxygen as an oxidant

Carl J. Mallia1, Paul M. Burton2, Alexander M. R. Smith2, Gary C. Walter2, Ian R. Baxendale1

  • 1 Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, United Kingdom
  • 2 Syngenta CP R&D Chemistry, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, United Kingdom
View abstract

Fine chemical syntheses under flow using SiliaCat catalysts

Rosaria Ciriminna a, Valerica Pandarus b, François Béland *b, Mario Pagliaro *a

  • * Corresponding authors a Istituto per lo Studio dei Materiali Nanostrutturati, CNR, via U. La Malfa 153, 90146 Palermo, Italy
  • b SiliCycle, 2500, Parc-Technologique Blvd, Québec, G1P 4S6 Canada
View abstract

The solid copper-mediated C-N cross-coupling of phenylboronic acids under continuous flow conditions

Jennifer Bao a, Geoffrey K. Tranmer a,b

  • a College of Pharmacy, Faculty of Health Science, University of Manitoba, Winnipeg, MB R3E 0T5, Canada
  • b Department of Chemistry, Faculty of Science, University of Manitoba, Winnipeg, MB R3T 2N2, Canada
View abstract

A Flow-based Synthesis of Telmisartan

Alex Martin, Ali Siamaki, Katherine Belecki, B. Gupton

  • Department of Chemistry and Department of Chemical and Life Science Engineering Virginia Commonwealth University 601 W. Main St. Richmond Virginia 23284 United States
View abstract

Continuous Synthesis of Organozinc Halides Coupled to Negishi Reactions

Nerea Alonso2,3, L. Zane Miller1, Juan de M. Muñoz2, Jesus Alcázar2,*, D. Tyler McQuade1,*

  • 1Department of Chemistry and Biochemistry, Florida State University, USA
  • 2Janssen Research and Development, Janssen-Cilag, Toledo, Spain
  • 3Facultad de Química, Universidad de Castilla-La Mancha, Spain
View abstract

Continuous Flow Synthesis of Thieno[2,3-c]isoquinolin-5(4H)-one Scaffold: A Valuable Source of PARP-1 Inhibitors

Paolo Filipponi, Carmine Ostacolo, Ettore Novellino, Roberto Pellicciari†§, Antimo Gioiello*†

  • Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo 1, I-06123 Perugia, Italy
  • Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Napoli, Italy §TES Pharma S.r.l., Corciano (Perugia), Italy
View abstract

Robust and reusable supported palladium catalysts for cross-coupling reactions in flow

William R. Reynoldsab, Pawel Plucinskibc, Christopher G. Frost*ab

  •   * Corresponding authors
  • a Centre for Sustainable Chemical Technologies, University of Bath, Claverton Down, Bath, UK
  • b Department of Chemistry, University of Bath, Claverton Down, Bath, UK
  • c Department of Chemical Engineering, University of Bath, Claverton Down, Bath, UK
View abstract

Flow-Based, Cerium Oxide Enhanced, Low-Level Palladium Sonogashira and Heck Coupling Reactions by Perovskite Catalysts

Claudio Battilocchio1, Benjamin N. Bhawal1, Rajeev Chorghade1, Benjamin J. Deadman1, Joel M. Hawkins2, Steven V. Ley1

  • 1 Innovative Technology Centre, Department of Chemistry, University of Cambridge, UK
  • 2 Pfizer Worldwide Research & Development, Groton, USA
View abstract

First Example of Alkyl-Aryl Negishi Cross-Coupling in Flow: Mild, Efficient and Clean Introduction of Functionalized Alkyl Groups

Brecht Egle2, Juan de Muñoz1, Nerea Alonso1, Wim M. De Borggraeve2, Antonio de la Hoz3, Angel Díaz-Ortiz3, Jesús Alcázar1

  • 1Janssen Research and Development Department of Medicinal Chemistry Janssen-Cilag, Toledo Spain
  • 2Department of Chemistry, Molecular Design and Synthesis University of Leuven, Heverlee Belgium
  • 3Universidad de Castilla-La Mancha Facultad de Ciencias y Tecnologías Químicas, Spain
View abstract

Synthesis of Carbohydrate-Functionalised Sequence-Defined Oligo(amidoamine)s by Photochemical ThiolEne Coupling in a Continuous Flow Reactor

Felix Wojcik1,2, Alexander G. O'Brien1,2, Sebastian Götze1,2, Peter H. Seeberger1,2, Laura Hartmann1,2

  • 1Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam (Germany)
  • 2Institute for Chemistry and Biochemistry, Freie Universität Berlin, Berlin (Germany)
View abstract

The Oxygen-Mediated Synthesis of 1,3-Butadiynes in Continuous Flow: Using Teflon AF-2400 to Effect Gas/Liquid Contact

Trine P. Petersen1,2,3, Anastasios Polyzos1,4, Matthew O’Brien1, Trond Ulven2, Ian R. Baxendale1, Steven V. Ley1

  • 1Whiffen Laboratory, University of Cambridge, UK
  • 2Department of Physics and Chemistry, University of Southern Denmark
  • 3Discovery Chemistry and DMPK, H. Lundbeck A/S,Denmark
  • 4CSIRO, Materials Science and Engineering, Australia
View abstract

Suzuki-Miyaura Cross-Coupling of Heteroaryl Halides and Arylboronic Acids in Continuous Flow

Timothy Noël, Andrew J. Musacchio

  • Department of Chemistry, MIT, USA
View abstract

Continuous Flow Coupling and Decarboxylation Reactions Promoted by Copper Tubing

Yun Zhang1, Timothy F. Jamison2, Sejal Patel1, Nello Mainolfi1, 1Novartis Institutes for Biomedical Research Inc., Cambridge, USA, 2MIT, Cambridge, USA

View abstract

Continuous Flow Palladium(II)-Catalyzed Oxidative Heck Reactions with Arylboronic Acids

Luke R. Odell1, Jonas Lindh1, Tomas Gustafsson2, Mats Larhed1*

  • 1Organic Pharmaceutical Chemistry, Department of MedChem, Uppsala University, Sweden
  • 2AstraZeneca R&D Mölndal, Sweden
View abstract

Application Notes regarding Coupling reactions

Application Note 49 – Suzuki Coupling with SiliaCat DPP-Pd Heterogeneous Catalyst

suzuki-coupling

In this application, a Vapourtec R-Series has been used to achieve rapid reaction times and high conversion of a Suzuki coupling, using a commercially available supported palladium catalyst. With a reaction time of just 1 min 15 seconds, it was possible to achieve yields of over 80%, at greater than 95% purity following a simple chromatographic separation. This application demonstrates how the Vapourtec R-Series can be used as a tool for the synthetic flow chemist, or for a development chemist beginning the scale up process.

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