Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01732d Click here for additional data file.

نویسندگان

  • Wengang Xu
  • Naohiko Yoshikai
چکیده

Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased steric bulk of the resulting ortho-substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion under peroxide photolysis or aerobic copper catalysis conditions. Overall, these two-step transformations offer convenient synthetic methods for ortho-functionalized benzonitriles.

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منابع مشابه

Rhodium-catalyzed C–H functionalization-based approach to eight-membered lactams† †Electronic supplementary information (ESI) available: Data for new compounds and experimental procedures and theoretical studies on mechanisms. CCDC 979559 and 990983. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00092k Click here for additional data file. Click here for additional data file.

Laboratory of Molecular Recognition an Zhejiang University, Hangzhou 310027, Zh ac.cn State Key Laboratory of Organometallic C Chemistry, Chinese Academy of Sciences, [email protected] Shanghai Key Laboratory of Magnetic Reson Normal University, Shanghai 200062, P. R. † Electronic supplementary information ( and experimental procedures and theor 979559 and 990983. For ESI and crystallo format s...

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Shanghai Key Laboratory of Green Chemi Chemistry and Molecular Engineering, Eas Zhongshan Road, Shanghai 200062, P. R. C Center for High Pressure Science and Tech Road, Shanghai 201203, P. R. China. E-mai State Key Laboratory of Superhard Materia Changchun, Jilin 130012, P. R. China † Electronic supplementary information bond data. CCDC 1428498. For ESI and electronic format see DOI: 10.1039/c6...

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017