Metal-mediated synthesis of a new heterocycle, 1-phenyl-phosphapyracene (, Ph-PyraPhos), by tandem phosphination/cyclization of peri-substituted 5-bromo-6-chloromethylacenaphthene () was investigated for comparison to Pt-catalyzed formation of 1-phosphaacenaphthenes (, AcePhos) from the analogous naphthalene precursor (). Reaction of PH2Ph with , NaOSiMe3 and a Cu catalyst gave ; a Pt catalyst yielded PHPh(CH2Ar) (, Ar = 5-Br-acenaphthyl). Deprotonation of a complex of this secondary phosphine, [Pt((R,R)-Me-DuPhos)(Ph)(PHPh(CH2Ar))][PF6] (), generated the phosphido intermediate Pt((R,R)-Me-DuPhos)(Ph)(PPhCH2Ar) (), which cyclized to give [Pt((R,R)-Me-DuPhos)(Ph)(Ph-PyraPhos)][PF6] (). Treatment of with silver triflate gave and the cyclometalated phosphine complex [Pt((R,R)-Me-DuPhos)(κ(2)-(P,C)-5-Ph2PCH2-6-C12H8)][PF6] (), which might form via Pt(iv) intermediates. The effects of the added "ace" bridge on structure and reactivity are discussed.
This research output has an Altmetric Attention Score of 2. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 26 May 2015.
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