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

ABSTRACT: A practical method for the deoxygenation of α-hydroxyl carbonyl compounds under mild reaction conditions is reported here. 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 α-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.

SUBMITTER: Xu X 

PROVIDER: S-EPMC9330554 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Na<sub>2</sub>S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products.

Xu Xiaobo X   Yan Leyu L   Zhang Zhi-Kai ZK   Lu Bingqing B   Guo Zhuangwen Z   Chen Mengyue M   Cao Zhong-Yan ZY  

Molecules (Basel, Switzerland) 20220722 15

A practical method for the deoxygenation of α-hydroxyl carbonyl compounds under mild reaction conditions is reported here. The use of cheap and easy-to-handle Na<sub>2</sub>S·9H<sub>2</sub>O as the reductant in the presence of PPh<sub>3</sub> and <i>N</i>-chlorosuccinimide (NCS) enables the selective dehydroxylation of α-hydroxyl carbonyl compounds, including ketones, esters, amides, imides and nitrile groups. The synthetic utility is demonstrated by the late-stage deoxygenation of bioactive mol  ...[more]

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