Jump to main content
Jump to site search

Issue 59, 2017
Previous Article Next Article

Nickel-catalysed direct alkylation of thiophenes via double C(sp3)–H/C(sp2)–H bond cleavage: the importance of KH2PO4

Author affiliations

Abstract

A Ni-catalyzed oxidative C–H/C–H cross-dehydrogenative coupling (CDC) reaction was developed for constructing various highly functionalized alkyl (aryl)-substituted thiophenes. This method employs thiophenes and aliphatic (aromatic) amides that contain an 8-aminoquinoline as a removable directing group in the presence of a silver oxidant. The approach enables the facile one-step synthesis of substituted thiophenes with high functional group compatibility via double C–H bond cleavage without affecting C–Br and C–I bonds. DFT calculations verify the importance of KH2PO4 as an additive for promoting C–H bond cleavage and support the involvement of a Ni(III) species in the reaction.

Graphical abstract: Nickel-catalysed direct alkylation of thiophenes via double C(sp3)–H/C(sp2)–H bond cleavage: the importance of KH2PO4

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Jun 2017, accepted on 30 Jun 2017 and first published on 30 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC04252C
Citation: Chem. Commun., 2017,53, 8316-8319
  •   Request permissions

    Nickel-catalysed direct alkylation of thiophenes via double C(sp3)–H/C(sp2)–H bond cleavage: the importance of KH2PO4

    X. Wang, P. Xie, R. Qiu, L. Zhu, T. Liu, Y. Li, T. Iwasaki, C. Au, X. Xu, Y. Xia, S. Yin and N. Kambe, Chem. Commun., 2017, 53, 8316
    DOI: 10.1039/C7CC04252C

Search articles by author

Spotlight

Advertisements