4.6 Article

Na2S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

Journal

MOLECULES
Volume 27, Issue 15, Pages -

Publisher

MDPI
DOI: 10.3390/molecules27154675

Keywords

deoxygenation; chlorination; dechlorination; one-pot

Funding

  1. National Natural Science Foundation of China and Henan province [22101096, K22029Y]
  2. Programs for Science and Technology Development of Henan Province [202102310329, 212102310329]
  3. Key Scientific Research Projects of Universities in Henan Province [19A150033]
  4. National Project Cultivation Foundation of Huanghuai University [XKPY-2019006]

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A practical method for the deoxygenation of alpha-hydroxyl carbonyl compounds under mild reaction conditions is reported. The use of cheap and easy-to-handle Na2S·9H2O as the reductant in the presence of PPh3 and N-chlorosuccinimide (NCS) enables the selective dehydroxylation of alpha-hydroxyl carbonyl compounds, including ketones, esters, amides, imides, and nitrile groups. The synthetic utility is demonstrated by the late-stage deoxygenation of bioactive molecule and complex natural products.
A practical method for the deoxygenation of alpha-hydroxyl carbonyl compounds under mild reaction conditions is reported here. The use of cheap and easy-to-handle Na2S center dot 9H(2)O as the reductant in the presence of PPh3 and N-chlorosuccinimide (NCS) enables the selective dehydroxylation of alpha-hydroxyl carbonyl compounds, including ketones, esters, amides, imides and nitrile groups. The synthetic utility is demonstrated by the late-stage deoxygenation of bioactive molecule and complex natural products.

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