Related Experiment Video
Updated: Oct 21, 2025
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Catalytic base-controlled regiodivergent heteronucleophilic hydrofunctionalization of β,γ-unsaturated amides
Yao Zhao1, Jiacheng Rui1, Qiang Du1
1Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China. iamxiaojinwu@njtech.edu.cn.
Abstract:
A general catalytic base-controlled regiodivergent nucleophilic hydrofunctionalization of both terminal and internal β,γ-unsaturated amides has been reported. The atom-economical addition of various S/P-based nucleophiles was also exclusively chemoselective. More than 60 branched or linear hetero-substituted aliphatic amides were synthesized from common starting materials under transition-metal-free conditions. Preliminary mechanistic studies are consistent with our proposed divergent catalytic cycles.
Related Concept Videos
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
01:27Aldol Condensation with β-Diesters: Knoevenagel Condensation
00:51Base-Promoted α-Halogenation of Aldehydes and Ketones
02:17Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
02:47Alkynes 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.
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration