Telescoped diazo transfer and rhodium-catalysed S–H insertion in continuous flow

Aoife M. Kearney; Denis Lynch; Stuart G. Collins; Anita R. Maguire

doi:10.1016/j.tetlet.2021.153438

Telescoped diazo transfer and rhodium-catalysed S–H insertion in continuous flow

Aoife M. Kearney
, Denis Lynch
, Stuart G. Collins
, Anita R. Maguire

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

Abstract

Rhodium-catalysed S–H insertion of α-diazo-γ-butyrolactams has been successfully telescoped using continuous processing with in situ generated triflyl azide in flow and deacylative diazo transfer, incorporating real-time reaction monitoring of the final process outflow by IR spectroscopy. Significantly, the α-diazo-γ-butyrolactam reaction stream was sufficiently pure to progress to the rhodium-catalysed S–H insertion step without detrimental impact on the rhodium catalyst or the reaction efficiency.

Original language	English
Article number	153438
Journal	Tetrahedron Letters
Volume	83
DOIs	https://doi.org/10.1016/j.tetlet.2021.153438
Publication status	Published - 26 Oct 2021

Keywords

Diazo transfer
Rhodium carboxylate catalyst
S–H insertion
Telescoped continuous processes
α-Diazolactams

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10.1016/j.tetlet.2021.153438

https://hdl.handle.net/10468/12424Licence: CC BY

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title = "Telescoped diazo transfer and rhodium-catalysed S–H insertion in continuous flow",

abstract = "Rhodium-catalysed S–H insertion of α-diazo-γ-butyrolactams has been successfully telescoped using continuous processing with in situ generated triflyl azide in flow and deacylative diazo transfer, incorporating real-time reaction monitoring of the final process outflow by IR spectroscopy. Significantly, the α-diazo-γ-butyrolactam reaction stream was sufficiently pure to progress to the rhodium-catalysed S–H insertion step without detrimental impact on the rhodium catalyst or the reaction efficiency.",

keywords = "Diazo transfer, Rhodium carboxylate catalyst, S–H insertion, Telescoped continuous processes, α-Diazolactams",

author = "Kearney, \{Aoife M.\} and Denis Lynch and Collins, \{Stuart G.\} and Maguire, \{Anita R.\}",

note = "Publisher Copyright: {\textcopyright} 2021 The Author(s)",

year = "2021",

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doi = "10.1016/j.tetlet.2021.153438",

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T1 - Telescoped diazo transfer and rhodium-catalysed S–H insertion in continuous flow

AU - Kearney, Aoife M.

AU - Lynch, Denis

AU - Collins, Stuart G.

AU - Maguire, Anita R.

PY - 2021/10/26

Y1 - 2021/10/26

N2 - Rhodium-catalysed S–H insertion of α-diazo-γ-butyrolactams has been successfully telescoped using continuous processing with in situ generated triflyl azide in flow and deacylative diazo transfer, incorporating real-time reaction monitoring of the final process outflow by IR spectroscopy. Significantly, the α-diazo-γ-butyrolactam reaction stream was sufficiently pure to progress to the rhodium-catalysed S–H insertion step without detrimental impact on the rhodium catalyst or the reaction efficiency.

AB - Rhodium-catalysed S–H insertion of α-diazo-γ-butyrolactams has been successfully telescoped using continuous processing with in situ generated triflyl azide in flow and deacylative diazo transfer, incorporating real-time reaction monitoring of the final process outflow by IR spectroscopy. Significantly, the α-diazo-γ-butyrolactam reaction stream was sufficiently pure to progress to the rhodium-catalysed S–H insertion step without detrimental impact on the rhodium catalyst or the reaction efficiency.

KW - Diazo transfer

KW - Rhodium carboxylate catalyst

KW - S–H insertion

KW - Telescoped continuous processes

KW - α-Diazolactams

UR - https://www.scopus.com/pages/publications/85116785774

U2 - 10.1016/j.tetlet.2021.153438

DO - 10.1016/j.tetlet.2021.153438

M3 - Article

AN - SCOPUS:85116785774

SN - 0040-4039

VL - 83

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153438

ER -

Telescoped diazo transfer and rhodium-catalysed S–H insertion in continuous flow

Abstract

Keywords

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