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Integrated Micro‐Flow Synthesis Based On Photochemical Wolff Rearrangement

Shinichiro Fuse, Yuma Otake, H. Nakamura
Published 2017 · Chemistry

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The Wolff rearrangement of α-diazo carbonyl compounds has remained important in organic synthesis since its development more than 115 years ago. The risks involved in handling diazo compounds can be minimized by utilizing micro-flow technology. In addition, photochemical Wolff rearrangement can be carried out efficiently with the aid of micro-flow technology. Integrated micro-flow synthesis is therefore well-suited to the preparation of α-diazo carbonyl compounds and their photochemical Wolff rearrangement. This review article summarizes recently reported micro-flow photochemical Wolff rearrangements and their application in integrated micro-flow syntheses.
This paper references
10.1021/acs.chemrev.5b00121
Modern Organic Synthesis with α-Diazocarbonyl Compounds.
A. Ford (2015)
10.1002/chem.201402801
Flow chemistry meets advanced functional materials.
R. Myers (2014)
10.1021/ACS.OPRD.5B00325
Flow Chemistry: Recent Developments in the Synthesis of Pharmaceutical Products
R. Porta (2016)
10.1002/ADSC.201100584
Flow Chemistry – A Key Enabling Technology for (Multistep) Organic Synthesis
Jens Wegner (2012)
10.1039/C0SC00381F
Continuous flow multi-step organic synthesis
Damien Webb (2010)
10.1039/c6cs00830e
Multi-step continuous-flow synthesis.
J. Britton (2017)
10.1021/OP100327D
Key Green Engineering Research Areas for Sustainable Manufacturing: A Perspective from Pharmaceutical and Fine Chemicals Manufacturers
C. Jiménez-González (2011)
10.1556/JFC-D-14-00015
Synthesis of N-Allyloxycarbonyl 3,5-Dihydroxyphenylglycine via Photochemical Wolff Rearrangement—Nucleophilic Addition Sequence in a Micro-Flow Reactor
Yuto Mifune (2014)
10.1021/acs.chemrev.5b00381
Homologation Reaction of Ketones with Diazo Compounds.
N. Candeias (2016)
10.1146/annurev.anchem.111808.073718
Integrated microreactors for reaction automation: new approaches to reaction development.
J. P. McMullen (2010)
10.1038/nchem.1753
The past, present and potential for microfluidic reactor technology in chemical synthesis.
K. Elvira (2013)
10.3390/molecules16097522
Recent Advances in Microflow Photochemistry
M. Oelgemöller (2011)
10.1002/JCTB.4012
The integration of flow reactors into synthetic organic chemistry
I. Baxendale (2013)
10.1021/OP200347K
Using Continuous Processes to Increase Production
N. G. Anderson (2012)
10.1002/cssc.201200766
Novel process windows for enabling, accelerating, and uplifting flow chemistry.
V. Hessel (2013)
10.1002/CEAT.201200009
Highlights of Photochemical Reactions in Microflow Reactors
M. Oelgemoeller (2012)
10.1002/cssc.201402874
Diazo compounds in continuous-flow technology.
Simon T. R. Mueller (2015)
10.1021/jo402849z
Continuous flow synthesis of α-halo ketones: essential building blocks of antiretroviral agents.
V. D. Pinho (2014)
10.3762/bjoc.11.134
The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry
M. Baumann (2015)
10.1021/OP4000169
Latest Highlights in Liquid-Phase Reactions for Organic Synthesis in Microreactors
L. Protasova (2013)
10.1002/chem.201404348
Taming hazardous chemistry in flow: the continuous processing of diazo and diazonium compounds.
Benjamin J. Deadman (2015)
10.1007/s11030-010-9282-1
The flow synthesis of heterocycles for natural product and medicinal chemistry applications
M. Baumann (2010)
10.1021/ja1050023
Enantiomerically pure trans-beta-lactams from alpha-amino acids via compact fluorescent light (CFL) continuous-flow photolysis.
Yvette M Vaske (2010)
10.1021/JA01167A101
An Improved Wolff Rearrangement in Homogeneous Medium1
M. Newman (1950)
10.1021/ol4027914
Continuous flow generation and reactions of anhydrous diazomethane using a Teflon AF-2400 tube-in-tube reactor.
F. Mastronardi (2013)
10.1039/c3cs60246j
Flow chemistry syntheses of natural products.
J. C. Pastre (2013)
10.1016/J.JPHOTOCHEMREV.2016.10.002
Utilization of microflow reactors to carry out synthetically useful organic photochemical reactions
Kazuhiko Mizuno (2016)
10.1021/jo402010b
Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.
Thomas P. Willumstad (2013)
10.1039/c0cc05060a
Ten key issues in modern flow chemistry.
J. Wegner (2011)
10.1071/CH15342
A Facile Preparation of α-Aryl Carboxylic Acid via One-Flow Arndt–Eistert Synthesis
Shinichiro Fuse (2015)
10.1002/chem.201400283
Photochemical transformations accelerated in continuous-flow reactors: basic concepts and applications.
Yuanhai Su (2014)
10.3762/bjoc.8.229
Flow photochemistry: Old light through new windows
J. P. Knowles (2012)
10.1021/jo500535f
Three in the spotlight: Photoinduced stereoselective synthesis of (Z)-acyloxyacrylamides through a multicomponent approach.
S. Garbarino (2014)
10.1002/cssc.201000271
Green and sustainable chemical synthesis using flow microreactors.
Jun-Ichi Yoshida (2011)
10.1016/0040-4039(96)00130-X
Homologation of carboxylic acids by arndt-eistert reaction under ultrasonic waves
Jean-Yves Winum (1996)
10.1002/tcr.201000020
Flash chemistry: flow microreactor synthesis based on high-resolution reaction time control.
Jun-Ichi Yoshida (2010)
10.1021/JO0017640
One-carbon homologation of carboxylic acids via BtCH(2)TMS: a safe alternative to the Arndt--Eistert reaction.
A. Katritzky (2001)
10.1039/C4RA08113G
Continuous flow synthesis of β-amino acids from α-amino acids via Arndt–Eistert homologation
V. D. Pinho (2014)
10.1021/acs.chemrev.5b00707
Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment.
Dario Cambié (2016)
10.1016/J.CEP.2016.02.008
Continuous-flow photochemistry: A need for chemical engineering
Karine Loubière (2016)
10.1002/IJCH.201400045
Photochemical Flow Reactions
E. M. Schuster (2014)
10.1002/9783527629114
Sustainable Industrial Chemistry
F. Cavani (2009)
10.1002/CBER.19350680142
Ein Verfahren zur berfhrung von Carbonsuren in ihre hheren Homologen bzw. deren Derivate
F. Arndt (1935)
10.1002/1099-0690(200207)2002:14<2193::AID-EJOC2193>3.0.CO;2-D
100 Years of the Wolff Rearrangement
W. Kirmse (2002)



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