Halogen-Bond-Catalyzed Addition of Carbon-Based Nucleophiles to N‑Acylimminium Ions

N-acylimminium ions are an important class of synthetic intermediates to produce diverse products upon treatment with different nucleophiles. Most of the reported catalytic protocol involved moisture-sensitive Lewis acids or transition metal. Herein, we reported an organocatalytic version by using h...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 14; pp. 5665 - 5669
Main Authors Chan, Yuk-Cheung, Yeung, Ying-Yeung
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.07.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUTION
ACTIVATION
CHEMISTRY
ORGANOCATALYSIS
EFFICIENT
ACYLIMINIUM IONS
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Summary:N-acylimminium ions are an important class of synthetic intermediates to produce diverse products upon treatment with different nucleophiles. Most of the reported catalytic protocol involved moisture-sensitive Lewis acids or transition metal. Herein, we reported an organocatalytic version by using halogen-bond catalyst as mild Lewis acid through anion-abstraction strategy. A preliminary result of enantioselective version by employing a chiral BINOL-phosphate anion has also been demonstrated.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02006