Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow

Yiding Chen; Marco Leonardi; Paul Dingwall; Ricardo Labes; Patrick Pasau; David C. Blakemore; Steven V. Ley

doi:10.1021/acs.joc.8b02721

Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow

Yiding Chen
, Marco Leonardi
, Paul Dingwall
, Ricardo Labes
, Patrick Pasau
, David C. Blakemore
, Steven V. Ley^*

^*Corresponding author for this work

Queen's University Belfast

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

490 Downloads (Pure)

Abstract

Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.

Original language	English
Pages (from-to)	15558-15568
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	83
Issue number	24
Early online date	16 Nov 2018
DOIs	https://doi.org/10.1021/acs.joc.8b02721
Publication status	Published - 21 Dec 2018

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.8b02721Licence: CC BY

Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow
Copyright 2018 the authors. This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 1.03 MBLicence: CC BY

Cite this

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abstract = "Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.",

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AU - Dingwall, Paul

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AU - Blakemore, David C.

AU - Ley, Steven V.

PY - 2018/12/21

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N2 - Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.

AB - Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.

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Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow

Abstract

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