Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 1, Pages 138-142Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500667
Keywords
alkynes; benzophosphole oxides; tert-butyl hydroperoxide; copper catalysts; secondary phosphine oxides
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Funding
- Chinese National Natural Science Foundation [21173178, 21232005, 21375113]
- National Basic Research Program of China [2012CB821600]
- Program for Changjiang Scholars and Innovative Research Team in University
- Fundamental Research Funds for the Central Universities [20720150049]
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Benzophosphole derivatives have attracted significant attention as promising organic optoelectronic materials. We have successfully developed a copper (2 mol%)/ tert-butyl hydroperoxide (2 equiv.) catalyst system for reaction of readily available secondary phosphine oxides and alkynes in acetonitrile at 60 degrees C under air, which provides a rapid access to a structurally diverse array of benzophosphole oxides in moderate to good yields within 30 min. The method can be easily used for a large-scale preparation. Preliminary mechanistic studies revealed that the addition of a phosphoryl radical onto a triple bond followed by cyclization on the phenyl moiety of the secondary phosphine oxide might occur to form the benzophosphole oxide.
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