Palladium(II)-catalyzed C–C and C–O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline N-oxides and nitroalkenes

Jiu-ling Li; Wei-ze Li; Ying-chun Wang; Qiu Ren; Heng-shan Wang; Ying-ming Pan

doi:10.1039/C6CC03530B

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Palladium(ii)-catalyzed C–C and C–O bond formation for the synthesis of C₁-benzoyl isoquinolines from isoquinoline N-oxides and nitroalkenes†

Jiu-ling Li,‡^a Wei-ze Li,‡^a Ying-chun Wang,^ab Qiu Ren,^a Heng-shan Wang*^a and Ying-ming Pan*^a

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* Corresponding authors

^a State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China
E-mail: whengshan@163.com, panym2013@hotmail.com

^b College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China

Abstract

C₁-Benzoyl isoquinolines can be generated via a palladium(II)-catalyzed C–C and C–O coupling of isoquinoline N-oxides with aromatic nitroalkenes. The reaction proceeds through remote C–H bond activation and subsequent intramolecular oxygen atom transfer (OAT). In this reaction, the N–O bond was designed as a directing group in the C–H bond activation as well as the source of an oxygen atom.

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Article information

DOI: https://doi.org/10.1039/C6CC03530B
Article type: Communication
Submitted: 27 Apr 2016
Accepted: 08 Jul 2016
First published: 14 Jul 2016

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Chem. Commun., 2016,52, 10028-10031

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Palladium(II)-catalyzed C–C and C–O bond formation for the synthesis of C₁-benzoyl isoquinolines from isoquinoline N-oxides and nitroalkenes

J. Li, W. Li, Y. Wang, Q. Ren, H. Wang and Y. Pan, Chem. Commun., 2016, 52, 10028 DOI: 10.1039/C6CC03530B

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