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C(sp3)–H dehydrogenation and C(sp2)–H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles

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Abstract

A novel and efficient synthesis of tetrahydropyridine (THP)-, dihydropyrrole (DHP)-, or tetrahydroazepine (THA)-3-carboxylates via cascade reactions of inactivated cyclic amines with CO and alcohols is presented. To our knowledge, this should be the first example in which functionalized N-heterocycles were prepared directly from Pd-catalyzed C(sp3)–H dehydrogenation and C(sp2)–H carbonylation of saturated cyclic amines. Moreover, the DHP-3-carboxylates thus obtained could readily undergo an oxidative aromatization to give pyrrole-3-carboxylates by using O2 as a green oxidant. Notable features of the methods developed herein include simple substrates, high efficiency and excellent atom-economy, mild reaction conditions, and broad substrate scope.

Graphical abstract: C(sp3)–H dehydrogenation and C(sp2)–H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles

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Publication details

The article was received on 25 Dec 2016, accepted on 20 Mar 2017, published on 20 Mar 2017 and first published online on 20 Mar 2017


Article type: Communication
DOI: 10.1039/C6CC10227A
Citation: Chem. Commun., 2017, Advance Article
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    C(sp3)–H dehydrogenation and C(sp2)–H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles

    Y. He, F. Wang, X. Zhang and X. Fan, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C6CC10227A

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