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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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Na2S-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 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 mol ...[more]

PMID: 35897854

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