Controlling the photochemical reactions of alkenes by light-path length effects of a microchannel reactor

Yamashita, Toshiaki; Matsushita, Shuhei; Nagatomo, Takuya; Yamauchi, Ryosuke; Yasuda, Masahide

doi:10.1007/s11164-012-0636-4

Cited by 8 publications

(2 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Paternó−Büchi reaction is a [2+2] photocycloaddition between an electronically excited carbonyl compound and an alkene leading to oxetanes . One of the earliest examples was the cycloaddition of 4‐penten‐1‐ol with acetone in a microchannel reactor irradiated with 313 nm light in aqueous solution . Kakiuchi and co‐workers studied the asymmetric Paternó−Büchi‐type photoreaction between 2,3‐dimethyl‐2‐butene and benzoylformic acid ester with a chiral menthyl auxiliary in a continuous‐flow microcapillary photoreactor.…”

Section: [2+2] Cycloadditions: 4‐membered Ringsmentioning

confidence: 99%

“…[83] One of the earliest examples was the cycloaddition of 4-penten-1-ol with acetone in a microchannel reactor irradiated with 313 nm light in aqueous solution. [84] Kakiuchi and co-workers studied the asymmetric PaternóÀ Büchi-type photoreaction between 2,3-dimethyl-2-butene and benzoylformic acid ester with a chiral menthyl auxiliary in a continuous-flow microcapillary photoreactor. Yields and enantiomeric excess were similar to batch conditions (around 50 % each), but the time needed to perform the reaction was decreased drastically using the flow reactor.…”

Section: The Paternó-büchi Reactionmentioning

confidence: 99%

See 1 more Smart Citation

Flow Chemistry for Cycloaddition Reactions

2020

View full text Add to dashboard Cite

Continuous flow reactors form part of a rapidly growing research area that has changed the way synthetic chemistry is performed not only in academia but also at the industrial level. This Review highlights the most recent advances in cycloaddition reactions performed in flow systems. Cycloadditions are atom-efficient transformations for the synthesis of carbo-and heterocycles, involved in the construction of challenging skeletons of complex molecules. The main advantages of translating these processes into flow include using intensified conditions, safer handling of hazardous reagents and gases, easy tuning of reaction conditions, and straightforward scaling up. These benefits are especially important in cycloadditions such as the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), Diels-Alder reaction, ozonolysis and [2 + 2] photocycloadditions. Some of these transformations are key reactions in the industrial synthesis of pharmaceuticals.

show abstract

Section: [2+2] Cycloadditions: 4‐membered Ringsmentioning

confidence: 99%

Section: The Paternó-büchi Reactionmentioning

confidence: 99%