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Issue 54, 2018
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Pd(II)-Catalyzed gamma-C(sp3)–H alkynylation of amides: selective functionalization of R chains of amides R1C(O)NHR

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Abstract

The gamma C(sp3)–H bond alkynylation of R chains of amides R1C(O)NHR, a fundamental class of synthetic substrates, has not been accomplished to date. Here, the first example of palladium(II)-catalyzed alkynylation of an unactivated gamma C(sp3)–H bond of alkyl amides (cyclic, linear, and amino acids) is reported. The kinetic experiment shows that the rate of the reaction depends on the coupling partners and the amides. Late-stage diversification of alkynylated amides was developed by utilizing amine and alkyne functionalities.

Graphical abstract: Pd(ii)-Catalyzed gamma-C(sp3)–H alkynylation of amides: selective functionalization of R chains of amides R1C(O)NHR

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Publication details

The article was received on 27 Apr 2018, accepted on 08 Jun 2018 and first published on 08 Jun 2018


Article type: Communication
DOI: 10.1039/C8CC03445A
Citation: Chem. Commun., 2018,54, 7483-7486
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    Pd(II)-Catalyzed gamma-C(sp3)–H alkynylation of amides: selective functionalization of R chains of amides R1C(O)NHR

    V. G. Landge, A. Parveen, A. Nandakumar and E. Balaraman, Chem. Commun., 2018, 54, 7483
    DOI: 10.1039/C8CC03445A

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