The First International Conference on
Automated Flow and Microreactor Synthesis(ICAMS-1)
January 18 to 20, 2018
Osaka, JapanPrograms

Organized by:Group for Research on Automated Flow and Microreactor Synthesis, Kinka Chemical
Society, Japan
Organizing Committee:
Jun-ichi Yoshida(Kyoto University)

Koichi Fukase(Osaka University)

Toshiyuki Iwai

(Osaka Research Institute of Industrial Science and Technology)

Kiyomi Kakiuchi(Nara Institute of Science and Technology)

Hirofumi Kuroda(Eisai Co., Ltd.)

Hitoshi Mitsui(MiChS Co., Ltd.)

Hajime Mori

(Industrial Technology Center of Wakayama Prefecture)

Akihiro Orita(Okayama University of Science)

Ilhyong Ryu(Osaka Prefecture University)

Tadahisa Sato

(Nano Innovation Laboratories Co., Ltd.)

Shoichi Shimizu(Nihon University)

Seiji Suga

(Okayama University)

Masashi Taga

(Kyowa Hakko Kirin Co., Ltd.)

Masami Takayama(Shionogi Co., Ltd.)

Masahiro Takeda(Sumitomo Chemical Co., Ltd.)

Hirotsugu Usutani(Takeda Pharmaceutical Co., Ltd.)

Executive Committee:
Aiichiro Nagaki(Kyoto University)

Takahide Fukuyama(Osaka Prefecture University)

Yoshiyuki Manabe(Osaka University)

Supported by:
Grant-in-Aid for Scientific Research (S) (No. 26220804)“Deeping and Developing New Aspects of Flash Chemistry.”
Kinka Chemical Society, Japan
Osaka Industrial Research Association
Kansai Branch, The Society of Chemical Engineers, JapanThe Japanese Society for Process Chemistry
The Society of Polymer Science, Japan (SPSJ) Kansai Regional Chapter
Kansai Branch, Chemical Society of JapanThe Pharmaceutical Society of Japan Kinki Branch
Kansai Branch, The Society of Synthetic Organic Chemistry, Japan

Program Summary
January 18 p.m.
13:00

January 19 a.m.

January 19 p.m.

9:00

Opening Remarks
10

January 20 a.m.
9:00

PL2 Timothy F. Jamison

KL5 Andrew Rutter

1010

PL1 Volker Hessel
202030

30

13:30

2040

4040

40

50

5050

50

14:00

10:0014:00

10:00

101010102020202030303030404050

5030

Poster Session
IL7 Hiroyuki Miyamura

KL2 Yangcheng Lu

IL8 Yasuhiro Nishiyama

IL1 Shinichiro Fuse
Coffee BreakIL2 Takashi Fukuyama
4040

Coffee Break50

50

PL4 Koichi Fukase

Coffee Break
15:00

11:00

1010

10

1020

20

20

15:00

KL3 Leslaw Mleczko

11:00

KL4 Joerg Sedelmeier

KL1 John R. Naber
2030

30

30

30

40

40

40

40

50

50

IL6 Yuichi Nakahara

PL3 C. Oliver Kappe

Closing Remarks

50

50

16:00

12:00

IL3 Heejin Kim
16:00

12:00

Lunch
1010102020303040404050

50

50

13:00

17:00

1010202030

30

IL4 Hiroaki Yasukouchi
2030

IL5 Hirotsugu Usutani

Dohgane Award
17:00

Banquet

40
50
18:00
10203040
50
19:00

All scientific program will be held at“Orbit Hall”, B1 floor, main building
Hotel Hankyu Expo Park
1-5 Senri-Banpaku-Koen, Suita-City, Osaka 565-0826, Japan

Program
January 18 (Thursday)
13:00-13:10

Opening Remarks

13:10-14:10

PL-1

Pharmaceutical Flow Chemistry: Multiple Steps in Multiple Flows
and in ONE-FLOW, with Smart On-line PAT-Quality Control
Volker Hessel (Eindhoven University of Technology, theNetherlands)

14:10-14:30

IL-1

Highly Efficient Amide Bond Formation Using Micro-flow
Technology
Shinichiro Fuse (Tokyo Institute of Technology, Japan)

14:30-14:50

IL-2

Application of Continuous Flow for the Synthesis of Eribulin
Mesylate
Takashi Fukuyama (Eisai Co.,Ltd., Japan)

14:50-15:10

Coffee Break

15:10-15:50

KL-1

Recent Applications in Flow Chemistry at MSD
John R. Naber (Merck & Co. Inc., USA)

15:50-16:10

IL-3

Control of Rapid Rearrangements and Synthetic Applications Using
Flow Microreactors
Heejin Kim (Kyoto University, Japan)

16:10-16:30

IL-4

Flow Reactor System for Phosgene Reaction
Hiroaki Yasukouchi (Kaneka Corp., Japan)

16:30-16:50

IL-5

Development and Scale-Up of a Flow Flash Chemistry Process for a
Key Boronic Acid Intermediate
Hirotsugu Usutani (Takeda Pharmaceutical Co., Ltd., Japan)

16:50-17:00

Dohgane Award CeremonyAwardee:David G. Cork (Formerly of Takeda Pharmaceutical Co., Japan)

January 19 (Friday)
9:00-10:00

PL-2

The When, Why, and How of Flow Chemistry
Timothy F. Jamison (Massachusetts Institute of Technology, USA)

10:00-10:40

KL-2

Micromixer Assisted Cationic Polymerization
Yangcheng Lu (Tsinghua University, China)

10:40-11:00

Coffee Break

11:00-11:40

KL-3

Technology Development for Continuous Synthesis of Fine
Chemicals - Industrial Perspective
Leslaw Mleczko (Bayer AG, Germany)

11:40-12:00

IL-6

Fundamental Technologies for Flow Microreactors -Accelerate theIndustrial ApplicationYuichi Nakahara (Ajinomoto Co., Inc., Japan)

12:00-13:30

Lunch

13:30-14:50

Poster Session

15:00-15:40

KL-4

Continuous Manufacturing at Novartis Pharma
Joerg Sedelmeier (Novartis Pharma AG, Switzerland)

15:40-16:40

PL-3

Organic Synthesis Goes Flow – The Use of Continuous Flow
Technology for the Synthesis of Active Pharmaceutical Ingredients
C. Oliver Kappe (University of Graz, Austria)

17:00-19:00

Banquet“Seiun”, 2nd floor, main building
Hotel Hankyu Expo ParkJanuary 20 (Saturday)
9:00-9:40

KL-5

The Evolution of Continuous Manufacturing Concepts for the
Manufacture of Active Pharmaceutical Ingredients
Andrew Rutter (GSK R&D, UK)

9:40-10:00

IL-7

Development of Heterogeneous Metal Nanoparticle Catalysts
toward Continuous-flow Reactions
Hiroyuki Miyamura (The University of Tokyo, Japan)

10:00-10:20

IL-8

Improvement of Photoreaction Efficiency in Flow Microreactors byusing Hg Lamp or Visible LED Lamp
Yasuhiro Nishiyama (Industrial Technology Center of Wakayama
Pref., Japan)

10:20-10:40

Coffee Break

10:40-11:40

PL-4

11:40-11:50

Closing Remarks

Synthesis of Biofucntional Glycans Using Integrated Reaction
Systems
Koichi Fukase (Osaka University, Japan)

Poster Presentations
PXX: ICAMS-1 Student Poster Award Nominee
P1

Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis ofPartial Structures
Tohru Oishi (Kyushu University)

P2

A Three-Minute Sequential Difunctionalization of 2,5-Norbornadiene Using Flow
Microreactor
Zuoyufan Yin (Osaka University), Heejin Kim (Kyoto University), Jun-ichi Yoshida(Kyoto University), Hidehiro Sakurai (Osaka University)

P3

Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acidic
Flash Switching in a Micro-flow Reactor
Yuma Otake (Tokyo Institute of Technology), Hiroyuki Nakamura (Tokyo Institute ofTechnology), Shinichiro Fuse (Tokyo Institute of Technology)

P4

Study of Aerobic Photooxidation with Slug-Flow Microreactor
Akichika Itoh (Gifu Pharmaceutical University), Yoshitomo
Pharmaceutical University)

Nagasawa(GifuP5

Phase-Transfer Catalyzed Nucleophilic Aromatic Substitution in a Continuous-flow
Microreactor
Hajime Mori (Industrial Technology Center of Wakayama Prefecture), Akane Saito(Industrial Technology Center of Wakayama Prefecture), Yasuhiro Nishiyama (Industrial
Technology Center of Wakayama Prefecture), Koji Machitani (Industrial Technology Centerof Wakayama Prefecture)

P6

Regioselective Intramolecular [2+2] Photocycloaddition of 1-Cyanonaphthalenes Bearing
Cycloalkenyl Groups Using Flow Microreactor
Kazuhiko Mizuno (Nara Institute of Science and Technology), Jiro Noguchi (NaraInstitute of Science and Technology), Momoe Nakano (Nara Institute of Science andTechnology), Yasuhiro Nishiyama (Ind. Tech. Center of Wakayama Pref.), Hajime Maeda(Kanazawa University), Kiyomi Kakiuchi (Nara Institute of Science and Technology)

P7

Improvement of Organic Photoreaction Efficiency by Difference of Refractive Index ofEach Segment in Slug Flow ModeJiro Noguchi (Nara Institute of Science and Technology), Momoe Nakano (Nara Instituteof Science and Technology), Yasuhiro Nishiyama (Nara Institute of Science andTechnology, Industrial Technology Center of Wakayama Prefecture), Kiyomi Kakiuchi(Nara Institute of Science and Technology)

P8

Flow Synthesis of Methanofullerene Derivative PCBM Using in situ Generated Sulfur
Ylide
Takatoshi Ito (Osaka Research Institute of Industrial Science and Technology), ToshiyukiIwai (Osaka Research Institute of Industrial Science and Technology), Shuhei Sumino(Osaka Research Institute of Industrial Science and Technology), Fukashi Matsumoto(Osaka Research Institute of Industrial Science and Technology), Yuta Inoue (RyukokuUniversity), Tetsuo Iwasawa (Ryukoku University), Takumi Mizuno (Osaka ResearchInstitute of Industrial Science and Technology), Toshinobu Ohno (Osaka Research Instituteof Industrial Science and Technology)

P9Synthesis of Diarenopentalenes: Consecutive in situ Preparation of Hydrogen Iodide andTransannulation of Sondheimer-Wong Diynes
Akihiro Orita (Okayama University of Science), Yasuhiro Okuda (Okayama University ofScience), Takanori Nishida (Okayama University of Science), Hirofumi Yamashita(Okayama University of Science), Takafumi Hagihara (Okayama University of Science)

P10

Continuous-Flow Dynamic Kinetic Resolution of Racemic Secondary Allyl Alcohols Usinga Single Packed-bed Reactor Containing Lipase and Oxovanadium
Dhiman Kundu (Osaka University), Satoko Katsuragi (Osaka University), Shigeaki
Masuda (Osaka University), Shuji Akai (Osaka University)

P11

Facile Procedure for Iron Catalyzed Cross-Coupling Reaction by a Microreactor
Koji Machitani (Industrial Technology Center of Wakayama Prefecture), Hajime Mori
(Industrial Technology Center of Wakayama Prefecture), Yasuhiro Nishiyama (Industrial
Technology Center of Wakayama Prefecture), Akane Saito (Industrial Technology Centerof Wakayama Prefecture), Yoshie Tanaka (Wakayama Medical University)

P12

Development of Flow Microwave Reactors with Solid State Microwave Source and Their
Application to High Speed Synthesis of Valuable Functional Materials
Takeko Matsumura (Minerva Light Laboratory LLC.), Kazunori Yamashita (Minerva
Light Laboratory LLC.), Atsushi Nakagawa (Finchems Inc. HQ plant and R&D)

P13

Microflow
Synthesis
andOrganic
Semiconductor
Characteristicsof
Alkyltetrathienonaphthalene
Hiroshi Ikeda (Osaka Prefecture University), Atsushi Yamamoto (Osaka PrefectureUniversity), Yasunori Matsui (Osaka Prefecture University), Toshio Asada (OsakaPrefecture University), Motoki Kumeda (Osaka Prefecture University), Kimiya Taniguchi(Osaka Prefecture University), Kenichiro Takagi (Osaka Prefecture University), YuSuenaga (Osaka Prefecture University), Kunihiko Nagae (Osaka Prefecture University),
Eisuke Ohta (Osaka Prefecture University), Hiroyasu Sato (Rigaku), Shiro Koseki (OsakaPrefecture University), Hiroyoshi Naito (Osaka Prefecture University)

P14

Green synthesis of α-amino acids by electrochemical carboxylation in a flow microreactor
Yang Qu (Yokohama National University), Chiaki Tsuneishi (Yokohama NationalUniversity), Hiroyuki Tateno (Yokohama National University), Yoshimasa Matsumura(Yamagata University), Mahito Atobe (Yokohama National University)

P15

Stereoselective Electrochemical Synthesis of Z-Alkenes from Alkynes Using a PEM
Reactor
Juri Minoshima (Yokohama National University), Atsushi Fukazawa (Yokohama NationalUniversity), Mahito Atobe (Yokohama National University), Yasushi Hashimoto (JXTG
Nippon Oil & Energy Co.), Yoshihiro Kobori (JXTG Nippon Oil & Energy Co.), Yasushi
Sato (JXTG Nippon Oil & Energy Co.)

P16

Axis-to-Center Chirality Transfer for the Synthesis of P-Stereogenic Organophosphorus
Compounds
Aya Sugiyama (Gifu University), Kazuma Kuwabara (Gifu University), Toshiaki Murai(Gifu University)

P17

Efficient Glycosylations Using Micro Fluidic SystemSeiji Masui (Osaka University), Yoshiyuki Manabe (Osaka University), Kento Tokunaga(Osaka University), Sianturi Julinton (Osaka University), Atsushi Shimoyama (OsakaUniversity), Takahide Fukuyama (Osaka Prefecture University), Ilhyong Ryu (OsakaPrefecture University), Koichi Fukase (Osaka University)

P18

Generation and Reactions of 2,2,2-Trifluoro-1-(phenylsulfonyl)ethyl Anion
Ryosuke Arai (Gunma University), Hiroyuki Murata (Gunma University), Aiichiro Nagaki(Kyoto University), Jun-ichi Yoshida (Kyoto University), Hideki Amii (Gunma University)

P19

Regio- and Stereoselective Carbozincation of Alkynyl Ethers Using Metal Halides and Silyl
EnolatesKyoungmin Kang (Osaka University), Kosuke Sakamoto (Osaka University), Yoshihiro
Nishimoto (Osaka University), Makoto Yasuda (Osaka University)

P20

Cyclopentene Annulation by Flow Process
Daisuke Domon (Hokkaido University), Aiichiro Nagaki (Kyoto University), Jun-ichi
Yoshida (Kyoto University), Keiji Tanino (Hokkaido University)

P21

Deprotonation of Dibromothiophenes Controlled by Flash Chemistry
Kentaro Okano (Kobe University), Yoshiki Yamane (Kobe University), Rikako Tada(Kobe University), Aiichiro Nagaki (Kyoto University), Jun-ichi Yoshida (KyotoUniversity), Atsunori Mori (Kobe University)

P22

Scalable Flow Synthesis of PCBM using a Flow Photo-Reactor with a Na Lamp
Mitsuhiro Ueda (Osaka Prefecture University), Naoyuki Imai (Showa Denko K.K),Shunsuke Yoshida (Showa Denko K.K), Hiroshi Yasuda (Showa Denko K.K), Takahide
Fukuyama (Osaka Prefecture University), Ilhyong Ryu (Osaka Prefecture University)

P23

Photoinduced Chemoselective Coupling Reaction of α-Bromo Ketones with Silyl Enol
Ether Catalyzed by an Organic Dye
Esumi Naoto (Osaka University), Kensuke Suzuki (Osaka University), Yoshihiro
Nishimoto (Osaka University), Makoto Yasuda (Osaka University)

P24

Three-step Sequential Continuous-flow Synthesis of rac-Pregabalin
Haruro Ishitani (The University of Tokyo), Kan Kanai (The University of Tokyo), Shu
Kobayashi (The University of Tokyo)

P25

Miniature in-Line Chiral Analyzer Based on Polarization-analyzing CMOS Image Sensor
Takashi Tokuda (Nara Institute of Science and Technology), Yasuto Mori (Nara Instituteof Science and Technology), Makito Haruta (Nara Institute of Science and Technology),
Toshihiko Noda (Nara Institute of Science and Technology), Kiyotaka Sasagawa (NaraInstitute of Science and Technology), Momoe Nakano (Nara Institute of Science andTechnology), Yasuhiro Nishiyama (Nara Institute of Science and Technology), Tsumoru
Morimoto (Nara Institute of Science and Technology), Kiyomi Kakiuchi (Nara Institute ofScience and Technology), Jun Ohta (Nara Institute of Science and Technology)

P26

Generation and Synthetic Applications of Trifluoromethyl Isobenzofurans
Shun Shinada (Gunma University), Masanori Inaba (Gunma University), Yoshimasa
Hikobe (Gunma University), Hideki Amii (Gunma University), Yuta Nishina (OkayamaUniversity)

P27

Synthesis of α-Alkylidene-β-Oxoimide using Flow System
Katuhiro Komuro (Waseda University), Hiroki Shimoda (Waseda University), Masahiro
Uwamori (Waseda University), Aiichiro Nagaki (Kyoto University), Jun-ichi Yoshida(Kyoto University), Masahisa Nakada (Waseda University)

P28

Catalytic Enantioselective Sequential C-C Bond Forming Reactions in Flow System
H.D.P. Wathsala (ISIR, Osaka University), Kenta Kishi (ISIR, Osaka University), Chen
Qingwen (ISIR, Osaka University), Shinobu Takizawa (ISIR, Osaka University), Hiroaki
Sasai (ISIR, Osaka University)P29[2+2] Cycloadditions of 1,3-Bifunctional Allenes with C60 by using a Flow Reaction
SystemHiroyuki Hashishita (Osaka Prefecture University) , Miho Hayama (Osaka PrefectureUniversity), Aiko Munechika (Osaka Prefecture University), Mitsuhiro Ueda (OsakaPrefecture University), Takahide Fukuyama (Osaka Prefecture University), Ilhyong Ryu(Osaka Prefecture University)

P30

Microflow Systems for the Organic Reactions Promoted by a Catalytic Amount ofElectricity
Seiji Suga (Okayama University), Hiroki Tanaka (Okayama University), Yuusuke
Kurihara, (Okayama University), Takayuki Hirata (Okayama University), Koichi Mitsudo(Okayama University)

P31

Synthetic Study of Dragmacidins via Decarboxylative Alkynylation Using Visible-LightMediated Photoredox Catalysis in a Flow System
Shota Kawakami (Keio University), Yohei Arai (Keio University), Zenyu Shiokawa (KeioUniversity), Takanori Matsumaru (Keio University), Shinsuke Inuki (Keio University,Kyoto University), Yukari Fujimoto (Keio University)

P32

Synthesis of Donor-Acceptor-Substituted Dye Having a Directing Group for Photoelectric
Conversion
Yasuhiro Okuda (Okayama University of Science), Takafumi Hagihara (OkayamaUniversity of Science), Takehiro Morimoto (Okayama University of Science), AkihiroOrita (Okayama University of Science)

P33

Magnetic Attachment of Lipase Immobilized on Bacteriogenic Iron Oxide Inside a
Microtube reactor for the Kinetic Resolution of Secondary Alcohols
Kyoko Mandai (Okayama University), Takehiro Fukuda (Okayama University), MiyazakiYuki (Okayama University), Hideki Hashimoto (Okayama University), Hiroki Mandai(Okayama University), Tadashi Ema (Okayama University), Jun Takada (Okayama
University, CREST JST), Seiji Suga (Okayama University)

P34

Novel Protocol for Chemoselective HalogenMetal Exchange on Cubane Using Dianiontype Zincate, R4ZnLi2Yumi Kato (Kyoto University), Seijiro Matsubara (Kyoto University)

P35

Efficient Synthesis of α-Gal Using One-Pot and Microfluidic Approaches for Developmentof a Novel Cancer Immunotherapy
Julinton Sianturi (Osaka University), Yoshiyuki Manabe (Osaka University), Kazuya
Kabayama (Osaka University), Koichi Fukase (Osaka University)

P36

Flow Amination of Functional Organolithiums: Design and Preparation of Aminating
Reagents Using Benchtop Stopped-Flow NMRYuya Yonekura (Kyoto University), Heejin Kim (Kyoto University), Jun-ichi Yoshida(Kyoto University)

P37

Selective Mono Addition of Aryllithiums to Dialdehydes by Micromixing
Hiroki Yamashita (Kyoto University), Yusuke Takahashi (Kyoto University), Satoshi
Ishiuchi, (Kyoto University) Keita Imai (Kyoto University), Aiichiro Nagaki (KyotoUniversity), Jun-ichi Yoshida (Kyoto University)

The First International Conference on
Automated Flow and Microreactor Synthesis(ICAMS-1)
January 18 to 20, 2018
Osaka, Japan

Exhibitions
13:00~17:00, January 18th
9:00~16:00, January 19th

Exhibitors List
Asahi Lab Commerce, Inc.
Blacktrace Japan Inc.
Device for FlowChemistry
DKSH Management Ltd.
Fuji Techno Industries Corporation
Junkosha Inc.
KOBE STEEL,Ltd.
MAKENGINEERING CORPORATION
M Technique Co., Ltd.
NARD Institute,Ltd.
Nippon Science Core Co.
Quality Design Co., Ltd.
SCRUM Inc.
TACMINA CORPORATIONTOKYO RIKAKIKAI CO., LTD.
YMC CO.,LTD.
TecnoApplications Co.,Ltd.