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Selective C-P(O) Bond Cleavage of Organophosphine Oxides by Sodium

Jian-Qiu Zhang, Eiichi Ikawa, Hiroyoshi Fujino, Yuki Naganawa, Yumiko Nakajima and Li-Biao Han*

*National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan, Email:

J.-Q. Zhang, E. Ikawa, H. Fujino, Y. Naganawa, Y. Nakajima, L.-B. Han, J. Org. Chem., 2020, 85, 14166-14173.

DOI: 10.1021/acs.joc.0c01642

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Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). A subsequent reaction with alkyl halides or with aryl halides in the presence of a Pd catalyst provides phosphine oxides in good to excellent yields.

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Key Words

Phosphine Oxides, Sodium

ID: J42-Y2020