Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl₃ promoted homocoupling

Scholarly Works

• Ichinari, D.; Ashikari, Y.; Mandai, K.; Aizawa, Y.; Yoshida, J.; Nagaki, A. A Novel Approach to Functionalization of Aryl Azides through the Generation and Reaction of Organolithium Species Bearing Masked Azides in Flow Microreactors. Angewandte Chemie 2019, 132, 1583–1587. doi:10.1002/ange.201912419
• Ichinari, D.; Ashikari, Y.; Mandai, K.; Aizawa, Y.; Yoshida, J.-i.; Nagaki, A. A Novel Approach to Functionalization of Aryl Azides through the Generation and Reaction of Organolithium Species Bearing Masked Azides in Flow Microreactors. Angewandte Chemie (International ed. in English) 2019, 59, 1567–1571. doi:10.1002/anie.201912419
• Nagaki, A. Recent topics of functionalized organolithiums using flow microreactor chemistry. Tetrahedron Letters 2019, 60, 150923. doi:10.1016/j.tetlet.2019.07.014
• Vasconcelos, S. N. S.; Reis, J. S.; de Oliveira, I. M.; Balfour, M. N.; Stefani, H. A. Synthesis of symmetrical biaryl compounds by homocoupling reaction. Tetrahedron 2019, 75, 1865–1959. doi:10.1016/j.tet.2019.02.001
• Shirejini, S. Z.; Mohammadi, A. Halogen–Lithium Exchange Reaction Using an Integrated Glass Microfluidic Device: An Optimized Synthetic Approach. Organic Process Research & Development 2017, 21, 292–303. doi:10.1021/acs.oprd.6b00307
• Schachtner, J.; Bayer, P.; von Wangelin, A. J. A flow reactor setup for photochemistry of biphasic gas/liquid reactions. Beilstein journal of organic chemistry 2016, 12, 1798–1811. doi:10.3762/bjoc.12.170
• Buter, J.; Heijnen, D.; Vila, C.; Hornillos, V.; Otten, E.; Giannerini, M.; Minnaard, A. J.; Feringa, B. L. Palladium-Catalyzed, tert-Butyllithium-Mediated Dimerization of Aryl Halides and Its Application in the Atropselective Total Synthesis of Mastigophorene A. Angewandte Chemie (International ed. in English) 2016, 55, 3620–3624. doi:10.1002/anie.201510328
• Buter, J.; Heijnen, D.; Vila, C.; Hornillos, V.; Otten, E.; Giannerini, M.; Minnaard, A. J.; Feringa, B. L. Palladium‐Catalyzed, tert‐Butyllithium‐Mediated Dimerization of Aryl Halides and Its Application in the Atropselective Total Synthesis of Mastigophorene A. Angewandte Chemie 2016, 128, 3684–3688. doi:10.1002/ange.201510328
• Itoh, T. DEVELOPMENT OF SOLVENT-DRIVEN IRON-CATALYZED REACTIONS. HETEROCYCLES 2016, 92, 1373–1395. doi:10.3987/rev-16-842
• Nagaki, A.; Yoshida, J.-i. Preparation and Use of Organolithium and Organomagnesium Species in Flow. Organometallic Flow Chemistry; Springer International Publishing, 2015; pp 137–175. doi:10.1007/3418_2015_154
• Ager, D. J. ACS Symposium Series - Managing Hazardous Reactions and Compounds in Process Chemistry. ACS Symposium Series; American Chemical Society, 2014; pp 285–351. doi:10.1021/bk-2014-1181.ch012
• Mleczko, L.; Zhao, D. ACS Symposium Series - Technology for Continuous Production of Fine Chemicals: A Case Study for Low Temperature Lithiation Reactions. ACS Symposium Series; American Chemical Society, 2014; pp 403–440. doi:10.1021/bk-2014-1181.ch015
• Shimizu, M. Lithium Compounds in Organic Synthesis; Wiley, 2014; pp 463–490. doi:10.1002/9783527667512.ch16
• Nagaki, A.; Yoshida, J.-i. Lithium Compounds in Organic Synthesis; Wiley, 2014; pp 491–512. doi:10.1002/9783527667512.ch17
• Wan, C.-F.; Chen, C.-S.; Hwang, K. C.; Lai, Y.-H.; Luo, J.-Y.; Liu, P.-C.; Fan, L.-S. Development and automation of microelectromechanical systems-based biochip platform for protein assay. Sensors and Actuators B: Chemical 2014, 193, 53–61. doi:10.1016/j.snb.2013.10.125
• Newby, J. A.; Huck, L.; Blaylock, D. W.; Witt, P. M.; Ley, S. V.; Browne, D. L. Investigation of a lithium-halogen exchange flow process for the preparation of boronates by using a cryo-flow reactor. Chemistry (Weinheim an der Bergstrasse, Germany) 2013, 20, 263–271. doi:10.1002/chem.201303736
• Kupracz, L.; Kirschning, A. Multiple Organolithium Generation in the Continuous Flow Synthesis of Amitriptyline. Advanced Synthesis & Catalysis 2013, 355, 3375–3380. doi:10.1002/adsc.201300614
• Protasova, L.; Bulut, M.; Ormerod, D.; Buekenhoudt, A.; Berton, J.; Stevens, C. V. Latest Highlights in Liquid-Phase Reactions for Organic Synthesis in Microreactors. Organic Process Research & Development 2013, 17, 760–791. doi:10.1021/op4000169
• Yılmaz, Ü.; Deniz, S.; Küçükbay, H.; Şireci, N. Microwave assisted Suzuki-Miyaura and Ullmann type homocoupling reactions of 2- and 3-halopyridines using a Pd(OAc)2/benzimidazolium salt and base catalyst system. Molecules (Basel, Switzerland) 2013, 18, 3712–3724. doi:10.3390/molecules18043712
• Kawamura, S.; Nakamura, M. Ligand-controlled Iron-catalyzed Cross Coupling of Benzylic Chlorides with Aryl Grignard Reagents. Chemistry Letters 2013, 42, 183–185. doi:10.1246/cl.2013.183

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