Exploiting the Continuous in situ Generation of Mesyl Azide for Use in a Telescoped Process

Rosella M. O'Mahony; Denis Lynch; Hannah L.D. Hayes; Eilís Ní Thuama; Philip Donnellan; Roderick C. Jones; Brian Glennon; Stuart G. Collins; Anita R. Maguire

doi:10.1002/ejoc.201700871

Exploiting the Continuous in situ Generation of Mesyl Azide for Use in a Telescoped Process

Rosella M. O'Mahony
, Denis Lynch
, Hannah L.D. Hayes
, Eilís Ní Thuama
, Philip Donnellan
, Roderick C. Jones
, Brian Glennon
, Stuart G. Collins
, Anita R. Maguire

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

Abstract

The hazardous diazo transfer reagent mesyl azide has been safely generated and used in situ for continuous diazo transfer as part of an integrated synthetic process with an embedded safety quench. Diazo transfer to β-keto esters and a β-ketosulfone was successful. In-line phase separation, by means of a continuous liquid–liquid separator, enabled direct telescoping with a thermal Wolff rearrangement.

Original language	English
Pages (from-to)	6533-6539
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	44
DOIs	https://doi.org/10.1002/ejoc.201700871
Publication status	Published - 1 Dec 2017

Keywords

Continuous flow
Diazo compounds
Flow Chemistry
Synthetic methods

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10.1002/ejoc.201700871

https://hdl.handle.net/10468/10769Licence: CC BY-NC-ND

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title = "Exploiting the Continuous in situ Generation of Mesyl Azide for Use in a Telescoped Process",

abstract = "The hazardous diazo transfer reagent mesyl azide has been safely generated and used in situ for continuous diazo transfer as part of an integrated synthetic process with an embedded safety quench. Diazo transfer to β-keto esters and a β-ketosulfone was successful. In-line phase separation, by means of a continuous liquid–liquid separator, enabled direct telescoping with a thermal Wolff rearrangement.",

keywords = "Continuous flow, Diazo compounds, Flow Chemistry, Synthetic methods",

author = "O'Mahony, \{Rosella M.\} and Denis Lynch and Hayes, \{Hannah L.D.\} and \{N{\'i} Thuama\}, Eil{\'i}s and Philip Donnellan and Jones, \{Roderick C.\} and Brian Glennon and Collins, \{Stuart G.\} and Maguire, \{Anita R.\}",

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doi = "10.1002/ejoc.201700871",

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T1 - Exploiting the Continuous in situ Generation of Mesyl Azide for Use in a Telescoped Process

AU - O'Mahony, Rosella M.

AU - Lynch, Denis

AU - Hayes, Hannah L.D.

AU - Ní Thuama, Eilís

AU - Donnellan, Philip

AU - Jones, Roderick C.

AU - Glennon, Brian

AU - Collins, Stuart G.

AU - Maguire, Anita R.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - The hazardous diazo transfer reagent mesyl azide has been safely generated and used in situ for continuous diazo transfer as part of an integrated synthetic process with an embedded safety quench. Diazo transfer to β-keto esters and a β-ketosulfone was successful. In-line phase separation, by means of a continuous liquid–liquid separator, enabled direct telescoping with a thermal Wolff rearrangement.

AB - The hazardous diazo transfer reagent mesyl azide has been safely generated and used in situ for continuous diazo transfer as part of an integrated synthetic process with an embedded safety quench. Diazo transfer to β-keto esters and a β-ketosulfone was successful. In-line phase separation, by means of a continuous liquid–liquid separator, enabled direct telescoping with a thermal Wolff rearrangement.

KW - Continuous flow

KW - Diazo compounds

KW - Flow Chemistry

KW - Synthetic methods

UR - https://www.scopus.com/pages/publications/85031700297

U2 - 10.1002/ejoc.201700871

DO - 10.1002/ejoc.201700871

M3 - Article

AN - SCOPUS:85031700297

SN - 1434-193X

VL - 2017

SP - 6533

EP - 6539

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 44

ER -

Exploiting the Continuous in situ Generation of Mesyl Azide for Use in a Telescoped Process

Abstract

Keywords

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