Facile synthesis of bisphosphine monoxides from Morita–Baylis–Hillman carbonates

GRAPHICAL ABSTRACT

ABSTRACT

A facile two-step synthesis of bisphosphine monoxides (BPMOs, with both the phosphine and phosphine oxide moieties within one molecule) from readily available Morita–Baylis–Hillman (MBH) carbonates was realized. Under the catalysis of DABCO, the MBH carbonates undergo allylic phosphorylation reaction with diphenylphosphine oxide or diethyl phosphonate to give monophosphine oxides bearing an activated alkene moiety; subsequent base-catalyzed hydrophosphination of the prepared monophosphine oxide with HPPh₂ readily affords the BPMOs.

KEYWORDS:

• Morita–Baylis–Hillman carbonates
• bisphosphine monoxides
• hydrophosphination
• allylic alkylation
• monophosphine oxides

Acknowledgments

The authors gratefully appreciate Professor Zhengjie He of Nankai University for his long-term support.

Funding

Financial support from the National Natural Science Foundation of China (Grant No. 21502135), the Natural Science Foundation of Shanxi (Grant No. 2014021015-3), and the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (Grant No. 2014114) is gratefully acknowledged.