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 cycload...

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Published inOrganic letters Vol. 20; no. 17; pp. 5282 - 5285
Main Authors Ayres, James N, Williams, Matthew T. J, Tizzard, Graham J, Coles, Simon J, Ling, Kenneth B, Morrill, Louis C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.09.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
CATALYZED CYANATION
ORGANIC-SYNTHESIS
CYCLOADDITION
CROSS-COUPLING REACTIONS
FACILE SYNTHESIS
HETEROCYCLES
AMINES
P-TOLUENESULFONAMIDE NCTS
ALLENAMIDES
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02225