Related Experiment Video
Updated: Mar 5, 2026

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
Published on: August 17, 2018
C(sp3)-H dehydrogenation and C(sp2)-H alkoxy carbonylation of inactivated cyclic amines towards functionalized
Yan He1, Fang Wang1, Xinying Zhang1
1School of Chemistry and Chemical Engineering, School of Environment, Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Henan Normal University, Xinxiang, Henan 453007, China. heyan@htu.cn xuesen.fan@htu.cn.
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.
Related Concept Videos
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Diazonium Group Substitution: –OH and –H
Amines to Alkenes: Hofmann Elimination
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
