A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds

Daniël S Verdoorn; Prabhat Ranjan; Tim de Reuver; Elwin Janssen; Christophe M L Vande Velde; Jordy M Saya; Bert U W Maes; Romano V A Orru

doi:10.1021/acs.orglett.3c00959

A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds

Daniël S Verdoorn
, Prabhat Ranjan
, Tim de Reuver
, Elwin Janssen
, Christophe M L Vande Velde
, Jordy M Saya^*
, Bert U W Maes^*
, Romano V A Orru^*

^*Corresponding author for this work

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

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Abstract

A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. Both the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt determine the selectivity toward the two products, i.e. 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imine versus 5-substituted-4-tosyl-2,4-dihydro-3H-1,2,4-triazol-3-one.

Original language	English
Pages (from-to)	4005-4009
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.3c00959
Publication status	Published - 9 Jun 2023

Keywords

Molecular Structure
Cobalt
Imines
Carboxylic Acids

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@article{e429ffa81a694d1a862a261f66408b2a,

title = "A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds",

abstract = "A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. Both the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt determine the selectivity toward the two products, i.e. 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imine versus 5-substituted-4-tosyl-2,4-dihydro-3H-1,2,4-triazol-3-one.",

keywords = "Molecular Structure, Cobalt, Imines, Carboxylic Acids",

author = "Verdoorn, \{Dani{\"e}l S\} and Prabhat Ranjan and \{de Reuver\}, Tim and Elwin Janssen and \{Vande Velde\}, \{Christophe M L\} and Saya, \{Jordy M\} and Maes, \{Bert U W\} and Orru, \{Romano V A\}",

year = "2023",

month = jun,

day = "9",

doi = "10.1021/acs.orglett.3c00959",

language = "English",

volume = "25",

pages = "4005--4009",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "22",

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TY - JOUR

T1 - A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds

AU - Verdoorn, Daniël S

AU - Ranjan, Prabhat

AU - de Reuver, Tim

AU - Janssen, Elwin

AU - Vande Velde, Christophe M L

AU - Saya, Jordy M

AU - Maes, Bert U W

AU - Orru, Romano V A

PY - 2023/6/9

Y1 - 2023/6/9

N2 - A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. Both the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt determine the selectivity toward the two products, i.e. 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imine versus 5-substituted-4-tosyl-2,4-dihydro-3H-1,2,4-triazol-3-one.

AB - A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. Both the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt determine the selectivity toward the two products, i.e. 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imine versus 5-substituted-4-tosyl-2,4-dihydro-3H-1,2,4-triazol-3-one.

KW - Molecular Structure

KW - Cobalt

KW - Imines

KW - Carboxylic Acids

U2 - 10.1021/acs.orglett.3c00959

DO - 10.1021/acs.orglett.3c00959

M3 - Article

C2 - 37224106

SN - 1523-7052

VL - 25

SP - 4005

EP - 4009

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds

Abstract

Keywords

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