Ni-Catalyzed Reductive Arylcyanation of Alkenes

We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyano-substituted oxindoles and isoquinoline-1,3-diones and features h...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 16; pp. 6466 - 6470
Main Authors Li, Hengxu, Chen, Jiachang, Dong, Jueqi, Kong, Wangqing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.2021
Amer Chemical Soc
Subjects
alkaloids
alkenes
Chemistry
Chemistry, Organic
enantioselectivity
Physical Sciences
rapid methods
Science & Technology
CYANATING AGENT
ARYL-ALKENYLATION
NITRILES
CYCLIZATION
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Summary:We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyano-substituted oxindoles and isoquinoline-1,3-diones and features high functional group tolerance. In addition, an enantioselective version was developed for the construction of enantiomerically enriched 3-cyanomethyl oxindole. This method has also been applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c02270