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Cobalt-Catalyzed Markovnikov Selective Sequential Hydrogenation/Hydrohydrazidation of Aliphatic Terminal Alkynes

Jieping Chen, Xuzhong Shen, Zhan Lu

2020Journal of the American Chemical Society76 citationsDOI

Abstract

Here, we reported for the first time a mechanistically distinctive cobalt-catalyzed Markovnikov-type sequential semihydrogenation/hydrohydrazidation of aliphatic terminal alkynes in one pot. A cobalt hydride species was employed as two roles for both a unique metal-catalyzed Markovnikov-type insertion of the aliphatic terminal alkynes and then metal-catalyzed hydrogen atom transfer of alkenes. This operationally simple protocol exhibits excellent functional group tolerance and step economy. The hydrazone products could be easily transferred to various valuable amine derivatives.

Topics & Concepts

Markovnikov's ruleChemistryCobaltCatalysisCombinatorial chemistryHydrideHydrazoneOrganic chemistryAmine gas treatingMetalRegioselectivityCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions
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