Continuous flow photolysis of aryl azides: Preparation of 3<i>H</i>-azepinones

Bou‐Hamdan, Farhan R.; Lévesque, François; O’Brien, Alexander G.; Seeberger, Peter H.

doi:10.3762/bjoc.7.129

Cited by 78 publications

(44 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…As a batch process, the photolysis of 2.0 g of methyl 4-azidobenzoate ( 98 , Scheme 33) in THF and water (0.05 M) had previously been reported to give a 45% yield in 20 hours, representing a productivity of 0.25 mmol/h [87]. Seeberger and workers have since revisited the reaction and, through the use of a continuous flow reactor, obtained 99 with a productivity of 0.84 mmol/h when irradiating the same substrate [88]. Flow conditions allowed for the precise control over the reaction time necessary to optimise this sensitive reaction.…”

Section: Reviewmentioning

confidence: 99%

Flow photochemistry: Old light through new windows

Knowles

Elliott²,

Booker‐Milburn³

2012

Beilstein J. Org. Chem.

367

190

View full text Add to dashboard Cite

SummarySynthetic photochemistry carried out in classic batch reactors has, for over half a century, proved to be a powerful but under-utilised technique in general organic synthesis. Recent developments in flow photochemistry have the potential to allow this technique to be applied in a more mainstream setting. This review highlights the use of flow reactors in organic photochemistry, allowing a comparison of the various reactor types to be made.

show abstract

Section: Reviewmentioning

confidence: 99%

Flow photochemistry: Old light through new windows

Knowles

Elliott²,

Booker‐Milburn³

2012

Beilstein J. Org. Chem.

367

190

View full text Add to dashboard Cite

show abstract

“…[170] Similarly,photolysis of aryl azides in the presence of water to give 3H-azepinones was reported. [171] …”

Section: Methodsmentioning

confidence: 99%

Continuous‐Flow Technology—A Tool for the Safe Manufacturing of Active Pharmaceutical Ingredients

Gutmann¹,

Cantillo²,

Kappe³

2015

Angew Chem Int Ed

1,270

676

View full text Add to dashboard Cite

In the past few years, continuous-flow reactors with channel dimensions in the micro- or millimeter region have found widespread application in organic synthesis. The characteristic properties of these reactors are their exceptionally fast heat and mass transfer. In microstructured devices of this type, virtually instantaneous mixing can be achieved for all but the fastest reactions. Similarly, the accumulation of heat, formation of hot spots, and dangers of thermal runaways can be prevented. As a result of the small reactor volumes, the overall safety of the process is significantly improved, even when harsh reaction conditions are used. Thus, microreactor technology offers a unique way to perform ultrafast, exothermic reactions, and allows the execution of reactions which proceed via highly unstable or even explosive intermediates. This Review discusses recent literature examples of continuous-flow organic synthesis where hazardous reactions or extreme process windows have been employed, with a focus on applications of relevance to the preparation of pharmaceuticals.

show abstract

“…The use of flow minimizes side reactions such as the formation of diazo compounds (Scheme 20) (81). This technique is a general method for lactam formation, however, some modification of reaction conditions will be needed.…”

Section: Scheme 19 Automated Flow Process For Aza-wittig Reaction Imentioning

confidence: 99%

Managing Hazardous Reactions and Compounds in Process Chemistry

Ager¹

2014

ACS Symposium Series

View full text Add to dashboard Cite

Continuous flow photolysis of aryl azides: Preparation of 3H-azepinones

Cited by 78 publications

References 50 publications

Flow photochemistry: Old light through new windows

Flow photochemistry: Old light through new windows

Continuous‐Flow Technology—A Tool for the Safe Manufacturing of Active Pharmaceutical Ingredients

Managing Hazardous Reactions and Compounds in Process Chemistry

Contact Info

Product

Resources

About