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Synthesis and reactivity of N-allenyl cyanamides

Synthesis and reactivity of N-allenyl cyanamides
Synthesis and reactivity of N-allenyl cyanamides

N-Allenyl cyanamides have been accessed via a one-pot deoxycyanamidation-isomerization approach using propargyl alcohol and N-cyano-N-phenyl-p-methylbenzenesulfonamide. The utility of this novel class of allenamide was explored through derivatization, with hydroarylation, hydroamination, and cycloaddition protocols employed to access an array of cyanamide products that would be challenging to access using existing methods.

1523-7060
5282-5285
Ayres, James N.
cc095fc1-1cd3-43e1-982f-a20556aa2010
Williams, Matthew T.J.
b0f899a3-e291-4085-9565-b141d79069dc
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Ling, Kenneth B.
054c3460-f666-4bfc-b5fd-7e56009c5522
Morrill, Louis C.
987789df-0246-46eb-80e0-79075392bb95
Ayres, James N.
cc095fc1-1cd3-43e1-982f-a20556aa2010
Williams, Matthew T.J.
b0f899a3-e291-4085-9565-b141d79069dc
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Ling, Kenneth B.
054c3460-f666-4bfc-b5fd-7e56009c5522
Morrill, Louis C.
987789df-0246-46eb-80e0-79075392bb95

Ayres, James N., Williams, Matthew T.J., Tizzard, Graham J., Coles, Simon J., Ling, Kenneth B. and Morrill, Louis C. (2018) Synthesis and reactivity of N-allenyl cyanamides. Organic Letters, 20 (17), 5282-5285. (doi:10.1021/acs.orglett.8b02225).

Record type: Article

Abstract

N-Allenyl cyanamides have been accessed via a one-pot deoxycyanamidation-isomerization approach using propargyl alcohol and N-cyano-N-phenyl-p-methylbenzenesulfonamide. The utility of this novel class of allenamide was explored through derivatization, with hydroarylation, hydroamination, and cycloaddition protocols employed to access an array of cyanamide products that would be challenging to access using existing methods.

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e-pub ahead of print date: 14 August 2018
Published date: 7 September 2018

Identifiers

Local EPrints ID: 426586
URI: http://eprints.soton.ac.uk/id/eprint/426586
ISSN: 1523-7060
PURE UUID: 303bb7eb-e74f-47f6-b67a-19cb6d365de4
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 30 Nov 2018 17:30
Last modified: 17 Dec 2019 01:54

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Contributors

Author: James N. Ayres
Author: Matthew T.J. Williams
Author: Simon J. Coles ORCID iD
Author: Kenneth B. Ling
Author: Louis C. Morrill

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