Commercial-Scale Visible Light Trifluoromethylation of 2-Chlorothiophenol Using CF3I Gas

被引：26

作者：

Harper, Kaid C. ^{[2
]}

Zhang, En-Xuan ^{[1
]}

Liu, Zhi-Qing ^{[1
]}

Grieme, Timothy ^{[2
]}

Towne, Timothy B. ^{[2
]}

Mack, Daniel J. ^{[2
]}

Griffin, Jeremy ^{[2
]}

Zheng, Song-Yuan ^{[1
]}

Zhang, Ning-Ning ^{[1
]}

Gangula, Srinivas ^{[1
]}

Yuan, Jia-Long ^{[1
]}

Miller, Robert ^{[2
]}

Huang, Ping-Zhong ^{[1
]}

Gage, James ^{[1
]}

Diwan, Moiz ^{[2
]}

Ku, Yi-Yin ^{[2
]}

机构：

[1] Asymchem Labs Tianjin Co Ltd, Tianjin 300457, Peoples R China

[2] Abbvie Proc Res & Dev, N Chicago, IL 60064 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2022年 / 26卷 / 02期

关键词：

photochemistry; photoredox; flow chemistry; continuous manufacturing; trifluoromethylation; PHOTOREDOX; PERFLUOROALKYLATION; POTENTIALS; CHEMISTRY;

D O I：

10.1021/acs.oprd.1c00436

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Despite the growth of photoredox methods in academia, application of photoredox at scale in the pharmaceutical and fine chemical industries has been slow. In this report, a photoredox trifluoromethylation of a thiophenol was modified from the original literature report, and the mechanism was investigated to define the key scale-up parameters. The mechanistic insight was leveraged in the design and execution of two different reactor designs: an LED-based plug flow photoreactor and a laser-based continuous stirred tank photoreactor. In one of the first examples of commercial-scale photoredox chemistry, the process was scaled to provide over 500 kg of the desired intermediate and amended to fully continuous manufacturing.

引用

页码：404 / 412

页数：9

共 42 条

[1] Reductive Alkylation of 2-Bromoazoles via Photoinduced Electron Transfer: A Versatile Strategy to Csp2-Csp3 Coupled Products
Arora, Amandeep
Teegardin, Kip A.
Weaver, Jimmie D.
[J]. ORGANIC LETTERS, 2015, 17 (15) : 3722 - 3725
[2] Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale
Beatty, Joel W.
Douglas, James J.
Miller, Richard
McAtee, Rory C.
Cole, Kevin P.
Stephenson, Corey R. J.
[J]. CHEM, 2016, 1 (03): : 456 - 472
[3] Development and Execution of a Production-Scale Continuous [2+2] Photocycloaddition
Beaver, Matthew G.
Zhang, En-xuan
Liu, Zhi-qing
Zheng, Song-yuan
Wang, Bin
Lu, Jiang-ping
Tao, Jian
Gonzalez, Miguel
Jones, Sian
Tedrow, Jason S.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2020, 24 (10) : 2139 - 2146
[4] Bogdan A. R., 2021, BURGERS MED CHEM DRU, P1
[5] Photons as a 21st century reagent
Bonfield, Holly E.
Knauber, Thomas
Levesque, Francois
Moschetta, Eric G.
Susanne, Flavien
Edwards, Lee J.
[J]. NATURE COMMUNICATIONS, 2020, 11 (01)
[6] Reagent and Catalyst Capsules: A Chemical Delivery System for Reaction Screening and Parallel Synthesis
Borlinghaus, Niginia
Kaschel, Johannes
Klee, Johanna
Haller, Vanessa
Schetterl, Jasmin
Heitz, Stephanie
Lindner, Tanja
Dietrich, Justin D.
Braje, Wilfried M.
Jolit, Anais
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (02) : 1357 - 1370
[7] Expanding the medicinal chemistry synthetic toolbox
Bostrom, Jonas
Brown, Dean G.
Young, Robert J.
Keseru, Gyorgy M.
[J]. NATURE REVIEWS DRUG DISCOVERY, 2018, 17 (10) : 709 - 727
[8] Manufacturing Process Development for Belzutifan, Part 2: A Continuous Flow Visible-Light-Induced Benzylic Bromination
Bottecchia, Cecilia
Levesque, Francois
McMullen, Jonathan P.
Ji, Yining
Reibarkh, Mikhail
Peng, Feng
Tan, Lushi
Spencer, Glenn
Nappi, Jarod
Lehnherr, Dan
Narsimhan, Karthik
Wismer, Michael K.
Chen, Like
Lin, Yipeng
Dalby, Stephen M.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (03) : 516 - 524
[9] Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry
Buglioni, Laura
Raymenants, Fabian
Slattery, Aidan
Zondag, Stefan D. A.
Noel, Timothy
[J]. CHEMICAL REVIEWS, 2022, 122 (02) : 2752 - 2906
[10] Continuous Manufacturing in Pharmaceutical Process Development and Manufacturing
Burcham, Christopher L.
Florence, Alastair J.
Johnson, Martin D.
[J]. ANNUAL REVIEW OF CHEMICAL AND BIOMOLECULAR ENGINEERING, VOL 9, 2018, 9 : 253 - 281

← 1 2 3 4 5 →