looks reasonabble. Pauson-Khand reaction are harder on di-substituted alkynes though and silicon has some special properties which could help the complexation observed in the reference you provide (see silicon's alpha and beta effects). Still worth a try I think.

The product you are after is quite unstable. In the absence of the steric bulk in the reported example I would expect it to react further with your substrates. There is a good chance it will just polymerise and make a mess.

Given the relative availability of the starting materials, you could just try it to see if it works.

Dear Eric B. J. Harris, now if we look the last discussion (How do you convert tetraphenylsilane to alkylbenzene?), once this cyclopentadienone would form in these conditions, whether the -silyl group can be substituted by the aromatic groups?

If you follow the reported synthesis and want to exchange the Silyl groups for phenyl groups, then you could try a Hiyama coupling with TBAF/Iodobenzene Pd2(dba)3 tBu3P.

The major concern here is the relative stability of your product, the parent cyclopentadienone has never been isolated and reactive intermediates featuring the cyclopentadienone moiety are unlikely to possess significant stability.

Dear Eric B. J. Harris, as you told, the Hiyama coupling can be performed to introduce the aryl group on the cyclopentadienone. But what about selectivity, means this substrate have Si attached with 2 phenyl and cyclopentadienone groups (in addition of allyl); all may equally participate for the coupling.

Is it the product that is of special interest to you or the reaction?

If it's the product, I don't think a Hiyama is the best way to go, at least not on this substrate. Hiyama coupling don't work so well with trialkylsilane (much better with a Metoxy-dialkylsilane). I don't think there is any stability issues with the product you are referiing to as there are multiple reports of it's synthesis in scifinder. Here's a patent procedure that looks simple enough and works on gram-scale:

[0021] Example 1 Synthesis of 2,3-dimethyl-1,4-diphenyl-1,3-cyclopentadienone Under nitrogen atmosphere, in a 300 ml three necked flask with a stirrer, dibenzyl ketone (110 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (13.2 mmol) in ethanol (110 mL) solution are stirred, butanedione (220 mmol) was added dropwise and disappearance of dibenzyl ketone was checked with gas chromatography, the solvent was distilled off by the evaporator. Pyridine (57 mL) and thionyl chloride (220 mmol) were added to the obtained mixture and the mixture was stirred. The reaction mixture was poured into ice water and the organic layer was extracted ether, dried and concentrated. It was purified by silica gel column chromatography and 3,4-dimethyl-2,5-diphenyl-2,4-cyclopentadienone was obtained (18.3 g, 64.2% of yield).

I agree with Pierre, if you are just after the product then the double aldol condensation is a much more sensible alternative and is generally how these systems are made.

But I am worried about alkyl diketone. In the presence of base, they are also prone for the deprotonation that would cause the formation of several side products. Generally in such double aldol type of cyclization, only aryl diketones has been used.

As long as the first bond formed is the condensation of dibenzyl ketone onto diacetyl, it will be fine. This is probably why in the procedure above they drop the diacetyl on the pre-formed enol. The second condensation should be much faster as it's intramolecular to form a 5 membered ring (at least 10 000 times faster than intermolecular). If it's reported in the litterature on multi-gram scale, you should definitely start by trying this rather than developping new reactions (if it's the product you want....).