Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 8, Pages 2143-2146Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202000716
Keywords
Semi-hydrogenation; Water; Transfer hydrogenation; Nickel; Alkyne
Categories
Funding
- National Natural Science Foundation of China [21961045, 21572198, 22061048]
- Applied Basic Research Project of Yunnan Province [2017FA004, 2018FB021]
- Basic Research Project of Chongqing Accademy of Chinese Materia Medica [jbky20190028]
- Yunnan Provincial Key Laboratory Construction Plan Funding of Universities
- Yunnan Provincial Engineering Research Center Construction Plan Funding of Universities
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A stereodivergent semi-hydrogenation of alkynes controlled by anions is reported, catalyzed by low-cost and stable nickel(II) salts with water as a friendly hydrogen source and zinc powder as a metal reductant. The anion of the nickel(II) salt plays a crucial role in controlling the stereoselectivity of the reaction, allowing for the convenient preparation of trans- and cis-alkenes under mild conditions. The reaction mechanism is proposed to involve water as the hydrogen donor based on control experiments.
An anion controlled stereodivergent semi-hydrogenation of alkynes is reported. The reactions are catalyzed by the low-cost and stable nickel(II) salts, using water as environmental friendly hydrogen source with zinc powder as metal reductant. Interestingly, the stereoselectivity of the reaction is well controlled by the anion of the nickel(II) salt. The present methodology allowed a low-cost and convenient preparation of trans- and cis-alkenes under mild conditions. The reaction mechanism is proposed with water as the hydrogen donor on the basis of the control experiments.
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